Advertisement

Sustainable Approaches Towards the Synthesis of Quinoxalines

  • Pradeep S. Jadhavar
  • Dinesh Kumar
  • Priyank Purohit
  • Bhavin V. Pipaliya
  • Asim Kumar
  • Srikant Bhagat
  • Asit K. ChakrabortiEmail author
Chapter

Abstract

The quinoxaline (Qx) nucleus is present in various bioactive molecules. Thus, synthesis of Qxs continues to draw the attention of synthetic organic/medicinal chemists. The contemporary interest in search for newer synthetic methods for this privileged class of compounds remains unabated and a vast number of publications continue to appear. The focus of this chapter is on the research works published in this area after the year 2000 with the inherent objective to attain sustainability towards the synthesis. The attention will be on the key sustainable approaches of pharmaceutical industries like the solvent-free reactions, use of alternate reaction media (e.g., water, fluorous alcohols, polyethylene glycols, and ionic liquids), and alternate modes of synthesis such as microwave-assisted synthesis and flow reactions.

Keywords

Quinoxaline Bioactivity Sustainable synthesis 

References

  1. 1.
    Carey JS, Laffan D et al (2006) Analysis of the reactions used for the preparation of drug candidate molecules. Org Biomol Chem 4:2337–2347Google Scholar
  2. 2.
    (a) González M, Cerecetto H (2012) Quinoxaline derivatives: a patent review. Expert Opin Ther Pat 22:1289–1302. (b) Rajurkar RM, Agrawal VA et al (2010) Heterocyclic chemistry of quinoxaline and potential activities of quinoxaline derivatives a review. Pharmacophore 1:65–76. (c) Patidar AK, Jeyakandan M et al (2011) Exploring potential of quinoxaline moiety. Intl J PharmTech Res 3:386–392. (d) Ingle RG, Marathe RP (2012) Review on litreture study of quinoxaline. Pharmacophore 3:109–116Google Scholar
  3. 3.
    (a) Sonawane ND, Rangnekar D (2002) Synthesis and application of 2-styryl-6,7-dichlorothiazolo[4,5-b]-quinoxaline based fluorescent dyes. J Heterocycl Chem 39:303–305. (b) Thomas KRJ, Velusamy M et al (2005) Chromophore-labeled quinoxaline derivatives as efficient electroluminescent materials. Chem Mater 17:1860–1866. (c) Dailey S, Feast JW et al (2001) Synthesis and device characterisation of side-chain polymer electron transport materials for organic semiconductor applications. J Mater Chem 11:2238–2240. (d) Sascha O, Rudiger F (2004) Quinoxalinodehydroannulenes: a novel class of carbon-rich materials. Synlett 15:1509–1512. (e) Brien OD, Weaver MS et al (1996) Use of poly (phenyl quinoxaline) as an electron transport material in polymer light-emitting diodes. Appl Phys Lett 69:881–883Google Scholar
  4. 4.
    (a) Galal SA, Abdelsamie AS (2013) Design, synthesis and structure activity relationship of novel quinoxaline derivatives as cancer chemopreventive agent by inhibition of tyrosine kinase receptor. Eur J Med Chem 69:115–124. (b) Lee SH, Kim S (2013) Anticancer effect of a quinoxaline derivative GK13 as a transglutaminase 2 inhibitor. J Cancer Res Clin 139:1279–1294. (c) Radhakrishnan P, Bryant VC (2013) Targeting the NF-κB and mTOR pathways with a quinoxaline urea analog that inhibits ikkβ for pancreas cancer therapy. Clin Cancer Res 19:2025–2035. (d) Noolvi MN, Patel HM (2011) Synthesis and in vitro antitumor activity of substituted quinazoline and quinoxaline derivatives: search for anticancer agent. Eur J Med Chem 46:2327–2346. (e) Chen Q, Bryant VC (2011) 2,3-Substituted quinoxalin-6-amine analogs as antiproliferatives: a structure–activity relationship study. Bioorg Med Chem Lett 21:1929–1932Google Scholar
  5. 5.
    (a) Sanna P, Carta A et al (1999) Preparation and biological evaluation of 6:7-trifluoromethyl(nitro)-6,7-difluoro-3-alkyl (aryl)-substituted-quinoxalin-2-ones. Part 3. IL Farmaco 54:169–177. (b) Ishikawa H, Sugiyama T et al (2012) Synthesis and antimicrobial activity of 2,3-bis(bromomethyl)quinoxaline derivatives. Bioorg Chem 41:1–5. (c) Ganapaty S, Ramalingam P et al (2008) Antimicrobial and antimycobacterial activity of some quinoxalines ‘N’ bridgehead heterocycles. Asian J Chem 20:3353–3356. (d) Seitz LE, Suling WJ et al (2002) Synthesis and antimycobacterial activity of pyrazine and quinoxaline derivatives. J Med Chem 45:5604–5606. (e) Vicente E et al (2011) Quinoxaline 1,4-di-N-oxide and the potential for treating tuberculosis infectious disorders. Drug Targets 11:196–204Google Scholar
  6. 6.
    Hui X, Desrivot J et al (2006) Synthesis and antiprotozoal activity of some new synthetic substituted quinoxalines. Bioorg Med Chem Lett 16:815–820Google Scholar
  7. 7.
    (a) Shibinskaya MO, Lyakhov SA (2010) Synthesis, cytotoxicity, antiviral activity and interferon inducing ability of 6-(2-aminoethyl)-6H-indolo[2,3-b]quinoxalines. Eur J Med Chem 45:1237–1243. (b) Wamberg MC, Hassan AA et al (2006) Intercalating nucleic acids (INAs) containing insertions of 6H-indolo[2,3-b]quinoxaline. Tetrahedron 62:11187–11199. (c) Wilhelmsson LM, Kingi N (2008) Interactions of antiviral indolo[2,3-b]quinoxaline derivatives with DNA. J Med Chem 51:7744–7750. (c) Ibrahim A, Masoudi AI (2008) Acyclic quinoxaline nucleosides synthesis and anti-HIV activity. Nucleos Nucleot Nucl 27:146–156Google Scholar
  8. 8.
    (a) Parra S, Laurentb F et al (2001) Imidazo[1,2-a]quinoxalines: synthesis and cyclic nucleotide phosphodiesterase inhibitory activity. Eur J Med Chem 36:255–264. b) Andrés J, Buijnsters P et al (2013) Discovery of a new series of [1,2,4]triazolo[4,3-a]quinoxalines as dual phosphodiesterase 2/phosphodiesterase 10 (PDE2/PDE10) inhibitors. Bioorg Med Chem Lett 23:785–790Google Scholar
  9. 9.
    Burguete A, Pontiki E et al (2011) Synthesis and biological evaluation of new quinoxaline derivatives as antioxidant and anti-inflammatory agents. Chem Biol Drug Des 77:255–267Google Scholar
  10. 10.
    a) Mamedov VA, Zhukova NA (2012) Progress in quinoxaline synthesis (Part 1). Prog Heterocycl Chem 24: 55–88. b) Mamedov VA, Zhukova NA (2013) Progress in quinoxaline synthesis (Part 2). Prog Heterocycl Chem 25:01–45Google Scholar
  11. 11.
    Nageswar YVD, Reddy KHV et al (2013) Recent developments in the synthesis of quinoxaline derivatives by green synthetic approaches. Org Prep Proced Int 45:1–27Google Scholar
  12. 12.
    (a) Cai J-J, Zou J-P et al (2008) Gallium(III) triflate-catalyzed synthesis of quinoxaline derivatives. Tetrahedron Lett 49:7386–7390. (b) Shi D-Q, Dou G-L et al (2008) An efficient synthesis of quinoxaline derivatives mediated by stannous chloride. J Heterocycl Chem 45:1797–1801Google Scholar
  13. 13.
    (a) Raw SA, Wilfred CD et al (2004) Tandem oxidation processes for the preparation of nitrogen-containing heteroaromatic and heterocyclic compounds. Org Biomol Chem 2:788–790. (b) Cho CS, Oh SG (2006) A new ruthenium-catalyzed approach for quinoxalines from o-phenylenediamines and vicinal-diols. Tetrahedron Lett 47:5633–5636. (c) Sithambaram S, Ding Y et al (2008) Manganese octahedral molecular sieves catalyzed tandem process for synthesis of quinoxalines. Green Chem 10:1029–1032. (d) Qi C, Jiang H et al (2011) DABCO-catalyzed oxidation of deoxybenzoins to benzils with air and one-pot synthesis of quinoxalines. Synthesis 3:387–396Google Scholar
  14. 14.
    Antoniotti S, Duñach E (2002) Direct and catalytic synthesis of quinoxaline derivatives from epoxides and ene-1,2-diamines. Tetrahedron Lett 43:3971–3973Google Scholar
  15. 15.
    (a) Mousset C, Provot O et al (2008) DMSO–PdI2 as a powerful oxidizing couple of alkynes into benzils: one-pot synthesis of nitrogen-containing five- or six-membered heterocycles. Tetrahedron 64:4287–4294. (b) Chandrasekhar S, Reddy NK et al (2010) Oxidation of alkynes using PdCl2/CuCl2 in PEG as a recyclable catalytic system: one-pot synthesis of quinoxalines. Tetrahedron Lett 51:3623–3625. (c) Tingol M, Mazzella M et al (2011) Elemental iodine or diphenyl diselenide in the [bis(trifluoroacetoxy)iodo]benzene-mediated conversion of alkynes into 1,2-diketones. Eur J Org Chem 2011:399–404Google Scholar
  16. 16.
    Poliakoff M, Licence P (2007) Sustainable technology: green chemistry. Nature 450:810–812Google Scholar
  17. 17.
    Alfonsi K, Colberg J et al (2008) Green chemistry tools to influence a medicinal chemistry and research chemistry based organization. Green Chem 10:31–36Google Scholar
  18. 18.
    Roughley SD, Jordan AM (2011) The medicinal chemist’s toolbox: an analysis of reactions used in the pursuit of drug candidates. J Med Chem 54:3451–3479Google Scholar
  19. 19.
    Tang SY, Bourne RA et al (2008) The 24 principles of green engineering and green chemistry: improvements productively. Green Chem 10:276–277Google Scholar
  20. 20.
    Herrerías CI, Xiaoquan Y et al (2007) Reactions of C–H bonds in water. Chem Rev 107:2546–2562Google Scholar
  21. 21.
    Tundo P, Anastas P et al (2000) Synthetic pathways and processes in green chemistry. Introductory overview. Pure Appl Chem 72:1207–1228Google Scholar
  22. 22.
    Constable DJC, Jimenez-Gonzalez C et al (2007) Perspective on solvent use in the pharmaceutical industry. Org Process Res Dev 11:133–137Google Scholar
  23. 23.
    (a) Metzger JO (1998) Solvent-free organic syntheses. Angew Chem Int Ed 37:2975–2978. (b) Tanaka K, Toda F (2000) Solvent-free organic synthesis. Chem Rev 100:1025–1075Google Scholar
  24. 24.
    Cave GWV, Raston CL et al (2001) Recent advances in solvent less organic reactions: towards benign synthesis with remarkable versatility. Chem Commun 21:2159–2169Google Scholar
  25. 25.
    (a) Toda F (1995) Solid state organic chemistry: efficient reactions, remarkable yields, and stereoselectivity. Acc Chem Res 28:480–486. (b) Ertl G (2008) Reactions at surfaces: from atoms to complexity (Nobel Lecture). Angew Chem Int Ed 47:3524–3535Google Scholar
  26. 26.
    (a) Singh MS, Chowdhury S (2012) Recent developments in solvent-free multicomponent reactions: a perfect synergy for eco-compatible organic synthesis. RSC Adv 2:4547–4592. (b) Candeias NR, Branco LC et al (2009) More sustainable approaches for the synthesis of N-based heterocycles. Chem Rev 109:2703–2802Google Scholar
  27. 27.
    Rothenberg G, Downie AP et al (2001) Understanding solid/solid organic reactions. J Am Chem Soc 123:8701–8708Google Scholar
  28. 28.
    (a) Sheldon RA (2000) Atom efficiency and catalysis in organic synthesis. Pure Appl Chem 72:1233–1246. (b) Clark JH (2001) Catalysis for green chemistry. Pure Appl Chem 73:103–111. (c) Sartori G, Maggi R (2006) Use of solid catalysts in Friedel-Crafts acylation reactions. Chem Rev 106:1077–1104Google Scholar
  29. 29.
    (a) Zhou C-H(C) (2010) Emerging trends and challenges in synthetic clay-based materials and layered double hydroxides. Appl Clay Sci 48:1–4. (b) Sharma G, Kumar R et al (2007) A novel environmentally friendly process for carbon-sulfur bond formation catalyzed by montmorillonite clays. J Mol Catal A: Chem 263:143–148. (c) Chankeshwara SV, Chakraborti AK (2006) Montmorillonite K-10 and Montmorillonite-KSF as new and reusable catalysts for conversion of amines to n-tert-butylcarbamates. J Mol Cat A: Chem 253:198–202. (d) Chakraborti AK, Kondaskar A et al (2004) Scope and limitations of Montmorillonite K-10 catalysed opening of epoxide rings by amines. Tetrahedron 60:9085–9091Google Scholar
  30. 30.
    Chakraborti AK, Rudrawar S et al (2004) An efficient synthesis of 2-amino alcohols by silica gel catalysed opening of epoxide rings by amines. Org Biomol Chem 2:1277–1280. (b) Chakraborti AK, Rudrawar S et al (2004) Lithium bromide as an inexpensive and efficient catalyst for opening of epoxide rings by amines at room temperature under solvent-free condition. Eur J Org Chem 2004(17):3597–3600Google Scholar
  31. 31.
    Usher CR, Michel AE, Grassian VH (2003) Reactions on Mineral Dust. Chem Rev 103:4883–4939Google Scholar
  32. 32.
    (a) Riego JM, Sedin Z et al (1996) Sulfuric acid on silica gel: an inexpensive catalyst for aromatic nitration. Tetrahedron Lett 37:513–516. (b) Chakraborti AK, Gulhane R (2003) Perchloric acid adsorbed on silica gel as new, highly efficient, and versatile catalyst for acetylation of phenols, thiols, alcohols, and amines. Chem Commun 1896–1897. (c) Chakraborti AK, Gulhane R (2003) Fluoroboric acid adsorbed on silica gel as a new and efficient catalyst for acylation of phenols, thiols, alcohols and amines. Tetrahedron Lett 44:3521–3525. (d) Chakraborti AK, Gulhane R (2003) Indian Patent 248506; Date: 20–07-2011. Appl. No. 266/DEL/2003Google Scholar
  33. 33.
    (a) Kumar D, Sonawane M et al (2013) Supported protic acid-catalyzed synthesis of 2,3-disubstituted thiazolidin-4-ones: enhancement of the catalytic potential of protic acid by adsorption on solid support. Green Chem 15:2872–2884. (b) Kumar D, Kommi DN et al (2013) Selectivity control during the solid supported protic acid catalysed synthesis of 1,2-disubstituted benzimidazoles and mechanistic insight to rationalize selectivity. RSC Adv 3:91–98. (c) Chakraborti AK, Singh B et al (2009) Protic acid immobilised on solid support as an extremely efficient recyclable catalyst system for a direct and atom economical esterification of carboxylic acids with alcohols. J Org Chem 74:5967–5974Google Scholar
  34. 34.
    Clark JH (1980) Fluoride ion as a base inorganic synthesis. Chem Rev 80:429–452Google Scholar
  35. 35.
    (a) Chakraborti AK, Sharma L et al (2002) The influence of hydrogen bonding in activation of nucleophile: phsh–(catalytic) kf in nmp as an efficient protocol for selective cleavage of alkyl/aryl esters and aryl alkyl ethers under nonhydrolytic and neutral conditions. J Org Chem 67:2541–2547. (b) Nayak MK, Chakraborti AK (1998) PhSH-(Catalytic) KF as an efficient protocol for chemoselective ester O-alkyl cleavage under non-hydrolytic condition. Chem Lett 297–298.Google Scholar
  36. 36.
    Kuarm BS, Crooks PA et al (2013) Tungstophosphoric acid supported on zirconia: a recyclable catalyst for the green synthesis on quinoxaline derivatives under solvent-free conditions. Phosphorus Sulfur Silicon 188:1071–1079Google Scholar
  37. 37.
    Ghorbani VR, Hajinazari S (2013) Poly-(N, N-dibromo-N-ethyl-benzene-1,3-disulphonamide) and N, N,N, N-tetrabromobenzene-1,3-disulphonamide as novel catalysts for synthesis of quinoxaline derivatives. J Chem Sci 125:353–358Google Scholar
  38. 38.
    Karami B, Khodabakhshib S et al (2012) A modified synthesis of some novel polycyclic aromatic phenazines and quinoxalines by using the tungstate sulfuric acid (tsa) as a reusable catalyst under solvent-free conditions. J Chin Chem Soc 59:187–192Google Scholar
  39. 39.
    Paul S, Basu B (2011) Synthesis of libraries of quinoxalines through eco-friendly tandem oxidation-condensation or condensation reactions. Tetrahedron Lett 52:6597–6602Google Scholar
  40. 40.
    Jafarpour M, Rezaeifard A et al (2011) Easy access to quinoxaline derivatives using alumina as an effective and reusable catalyst under solvent-free conditions. Applied Catalysis A: General 394:48–51Google Scholar
  41. 41.
    Nandi GC, Samai S (2011) Silica-gel-catalysed efficient synthesis of quinoxaline derivatives solvent- free conditions. Synth Commun 41:417–425Google Scholar
  42. 42.
    Jun L, Jiang DN et al (2011) Eco-friendly synthesis of quinoxaline derivatives by grinding under solvent-free conditions. J Heterocyclic Chem 48:403–406Google Scholar
  43. 43.
    Ahmad S, Ali M (2007) Efficient solid acid promoted synthesis of quinoxaline derivatives at room temperature. Chin J Chem 25:818–821Google Scholar
  44. 44.
    Hi DQ, Lan G (2008) Efficient synthesis of quinoxaline derivatives catalyzed by p-toluenesulfonic acid under solvent-free conditions. Synth Commun 38:3329–3337Google Scholar
  45. 45.
    Kuarma S, Peter A et al (2013) An expeditious synthesis of quinoxalines by using biodegradable cellulose sulfuric acid as a solid acid catalyst. Green Chem Lett Rev 6:228–232Google Scholar
  46. 46.
    Ghosh P, Mandal A et al (2013) γ-Maghemite-silica nanocomposite: a green catalyst for diverse aromatic N-heterocycles. Catal Commun 41:146–152Google Scholar
  47. 47.
    Yun-fei J, Tang-ming C et al (2012) Ga(ClO4)3-catalyzed reaction of 1,2-diamines and α-bromoketones: synthesis of 2-substituted quinoxalines. Chem Res Chin Univ 28:642–646Google Scholar
  48. 48.
    Das B, Venkateswarlu K et al (2007) An efficient and convenient protocol for the synthesis of quinoxalines and dihydropyrazines via cyclization–oxidation processes using HClO4/SiO2 as a heterogeneous recyclable catalyst. Tetrahedron Lett 48:5371–5374Google Scholar
  49. 49.
    Gao L, Liu R, Yu C et al (2013) NHC-initiated cascade, metal-free synthesis of quinoxaline derivatives under solvent-free conditions. Res Chem Intermed. 40:2131–2138Google Scholar
  50. 50.
    Haldar P, Dutta B et al (2007) Uncatalyzed condensation between aryl-1,2-diamines and diethyl bromomalonate: a one-pot access to substituted ethyl 3-hydroxyquinoxaline-2-carboxylates. Tetrahedron Lett 48:5855–5857Google Scholar
  51. 51.
    (a) Adams DJ, Dyson PJ (2004) Chemistry in alternative reaction media. Wiley, England. (b) Sheldon RA (2005) Green solvents for sustainable organic synthesis: state of the art. Green Chem 7:267–278. (c) Capello C, Fischer U et al (2007) What is a green solvent? A comprehensive framework for the environmental assessment of solvents. Green Chem 9:927–934. (d) Hailes HC (2007) Reaction solvent selection: the potential of water as a solvent for organic transformations. Org Process Res Dev 11:114–120Google Scholar
  52. 52.
    Diels O, Alder K (1931) Synthesen in der hydroaromatischen Reihe. XII. Mitteilung. („Dien-Synthesen” sauerstoffhaltiger Heteroringe. 2. Dien-Synthesen des Furans.). Ann Chem 490:243–245Google Scholar
  53. 53.
    Rideout DC, Breslow R (1980) Hydrophobic acceleration of Diels-Alder reactions. J Am Chem Soc 102:7816–7817Google Scholar
  54. 54.
    (a) Lindström UM (2002) Stereoselective organic reactions in water. Chem Rev 102:2751–2772. (b) Li CJ (2005) Organic reactions in aqueous media with a focus on carbon-carbon bond formations: a decade update. Chem Rev 105:3095–3165. (c) Li CJ, Chen L (2006) Organic chemistry in water. Chem Soc Rev 35:68–82. (d) Minakata S, Komatsu M (2009) Organic reactions on silica in water. Chem Rev 109:711–724. (e) Chanda A, Fokin VV (2009) Organic synthesis “on water”. Chem Rev 109:725–748. (f) Butler RN, Coyne AG (2010) Water: nature’s reaction enforcer—comparative effects for organic synthesis “in-water” and “on-water”. Chem Rev 110:6302–6337. (g) Gawande MB, Bonifa´cio VDB et al (2013) Benign by design: catalyst-free in-water, on-water green chemical methodologies in organic synthesis. Chem Soc Rev 42:5522–5551Google Scholar
  55. 55.
    (a) Narayan S, Muldoon J et al (2005) “On water”: unique reactivity of organic compounds in aqueous suspension. Angew Chem Int Ed 44:3275–3279. (b) Jung Y, Marcus RA (2007) On the theory of organic catalysis “on water”. J Am Chem Soc 129:5492–5502. (c) Beattie JK, McErlean CSP et al (2010) The mechanism of on-water catalysis. Chem Eur J 16:8972–8974. (d) Mellouli S, Bousekkine L et al (2012) Investigation of “on water” conditions using a biphasic fluidic platform. Angew Chem Int Ed 51:7981–7984Google Scholar
  56. 56.
    Hayashi Y (2006) In water or in the presence of water? Angew Chem Int Ed 45:8103–8104Google Scholar
  57. 57.
    Shapiro N, Vigalok A (2008) Highly efficient organic reactions “on water”, “in water”, and both. Angew Chem Int Ed 47:2849–2852Google Scholar
  58. 58.
    (a) Breslow R (1991) Hydrophobic effects on simple organic reactions in water. Acc Chem Res 24:159–164. (b) Breslow R (2004) Determining the geometries of transition states by use of antihydrophobic additives in water. Acc Chem Res 37:471–478. (c) Dr. Lindström UM, Andersson F (2006) Hydrophobically directed organic synthesis. Angew Chem Int Ed 45:548–551Google Scholar
  59. 59.
    (a) Otto S, Engberts J, B N F (2000) Diels Alder reactions in water. Pure Appl Chem 72:1365–1372. (b) Otto S, Blokijl W et al (1994) Diels-Alder reactions in water. Effects of hydrophobicity and hydrogen bonding. J Org Chem 59:5372–5376. (c) Van der wel GK, Wijnen JW et al (1996) Solvent effects on a Diels–Alder reaction involving a cationic diene: consequences of the absence of hydrogen-bond interactions for accelerations in aqueous media. J Org Chem 61:9001–9005. (d) Chandrasekhar J, Shariffskul S et al (2002) QM/MM simulations for Diels–Alder reactions in water: contribution of enhanced hydrogen bonding at the transition state to the solvent effect. J Phys Chem B 106(33):8078–8085. (e) Aggarwal VK, Dean DK et al (2002) Rate acceleration of the Baylis–Hillman reaction in polar solvents (water and formamide). Dominant Role Of Hydrogen Bonding, Not Hydrophobic Effects, Is Implicated. J Org Chem 67:510–514Google Scholar
  60. 60.
    (a) Pirrung MC (2006) Acceleration of Organic Reactions through Aqueous Solvent Effects. Chem Eur J 12:1312–1317. (b) Pirrung MC, Das Sarma K (2005) Aqueous medium effects on multi-component reactions. Tetrahedron 61:11456–11472Google Scholar
  61. 61.
    (a) Chankeshwara SV, Chakraborti AK (2006) Catalyst-free chemoselective n-tert-butyloxycarbonylation of amines in water. Org Lett 8:3259–3262. (b) Khatik GL, Kumar R et al (2006) Catalyst-free conjugated addition of thiols to α,β-unsaturated carbonyl compounds in water. Org Lett 8:2433. (c) Chakraborti AK, Rudrawar S et al (2007) “On water” organic synthesis: a highly efficient and clean synthesis of 2-aryl/heteroaryl/styryl benzothiazoles and 2-alkyl/aryl alkyl benzothiazolines. Green Chem 9:1335–1340Google Scholar
  62. 62.
    Vöhringer-Martinez E, Hansmann B et al (2007) Water catalysis of a radical-molecule gas-phase. Science 315:497–501Google Scholar
  63. 63.
    (a) Vilotijevic I, Jamison TF (2007) Epoxide-opening cascades promoted by water. Science 317:1189–1192. (b) Byers JA, Jamison TF (2013) Entropic factors provide unusual reactivity and selectivity in epoxide-opening reactions promoted by water. Proc Natl Acad Sci 110:16724–16729Google Scholar
  64. 64.
    (a) Kommi DN, Kumar D et al (2012) “All-water” chemistry of tandem N-alkylation–reduction–condensation for synthesis of N-arylmethyl-2-substituted benzimidazoles. Green Chem 14:3329–3335. (b) Kommi DN, Jadhavar PS et al (2013) “All-water” one-pot diverse synthesis of 1,2-disubstitutedbenzimidazoles: hydrogen bond driven ‘synergistic electrophile–nucleophile dual activation’ by water. Green Chem 15:798–810. (c) Kommi DN, Kumar D, Chakraborti AK (2013) “All water chemistry” for a concise total synthesis of the novel class anti-anginal drug (RS), (R), and (S)-ranolazine. Green Chem 15:756–767. (d) Kommi DN, Kumar D et al (2013) Protecting group-free concise synthesis of (RS)/(S)-lubeluzole. Org Lett 15:1158–1161Google Scholar
  65. 65.
    (a) Sharma G, Kumar R et al (2008) ‘On water’ synthesis of 2,4-diaryl-2,3-dihydro-1,5-benzothiazepines catalysed by sodium dodecyl sulfate (SDS). Tetrahedron Lett 49:4269–4271. (b) Holmberg K (2007) Organic reactions in microemulsions. Eur J Org Chem 2007(5):731–742. (c) Shiri M, Zolfigol MA (2008) Surfactant-type catalysts in organic reactions. Tetrahedron 65:587–598. (d) Parikh N, Kumar D et al (2011) Surfactant mediated oxygen reuptake in water for green aerobic oxidation: mass-spectrometric determination of discrete intermediates to correlate oxygen uptake with oxidation efficiency. J Chem Soc Chem Commun 47:1797–1799Google Scholar
  66. 66.
    (a) Kobayashi S, Wakabayashi T et al (1997) Lewis acid catalysis in micellar systems. Sc(OTf)3-catalyzed aqueous aldol reactions of silyl enol ethers with aldehydes in the presence of a surfactant. Tetrahedron Lett 38:4559–4562. (b) Kobayashi S, Wakabayashi T (1998) Scandium trisdodecylsulfate (STDS). A new type of lewis acid that forms stable dispersion systems with organic substrates in water and accelerates aldol reactions much faster in water than in organic solvents. Tetrahedron Lett 39:5389–5392. (c) Manabe K, Kobayashi S (1999) Effects of metal cations in lewis acid-surfactant combined catalyst-mediated aldol reactions in water. Synlett 1999(5):547–548. (d) Manabe K, Mori Y et al (1999) Effects of Lewis acid-surfactant-combined catalysts on aldol and diels-alder reactions in water. Tetrahedron 55:11203–11208. (e) Kobayashi S, Mori Y et al (1999) Catalytic asymmetric aldol reactions in water using a chiral Lewis acid–surfactant-combined catalyst. Green Chem 1:175–177. (f) Kobayashi S, Manabe K (2002) Development of novel Lewis acid catalysts for selective organic reactions in aqueous media. Acc Chem Res 35:209–217Google Scholar
  67. 67.
    Parikh N, Kumar D et al (2011) Surfactant mediated oxygen reuptake in water for green aerobic oxidation: mass-spectrometric determination of discrete intermediates to correlate oxygen uptake with oxidation efficiency. J Chem Soc Chem Commun 47:1797–1799Google Scholar
  68. 68.
    More SV, Sastry MNV et al (2006) Cerium (IV) ammonium nitrate (CAN) as a catalyst in tap water: a simple, proficient and green approach for the synthesis of quinoxalines. Green Chem 8:91–95Google Scholar
  69. 69.
    Hazarika P, Gogoia P et al (2007) efficient and green method for the synthesis of 1,5-benzodiazepine and quinoxaline derivatives in water. Synth Commun 37:3447–3445Google Scholar
  70. 70.
    Heravi M, Taheri S et al (2007) On water: a practical and efficient synthesis of quinoxaline derivatives catalyzed by CuSO4.5H2O. Catal Commun 8:211–214Google Scholar
  71. 71.
    Yadav JS, Reddy S et al (2008) Bismuth(III)-catalyzed rapid synthesis of 2,3-disubstituted quinoxalines in water. Synthesis 23:3787–3792Google Scholar
  72. 72.
    Huang TK, Wang R et al (2008) Montmorillonite K-10: an efficient and reusable catalyst for the synthesis of quinoxaline derivatives in water. Catal Commun 9:1143–1147Google Scholar
  73. 73.
    Hasaninejad A, Zare A et al (2009) Zirconium tetrakis (dodecyl sulfate)[Zr(DS)4] as an efficient Lewis acid-surfactant combined catalyst for the synthesis of quinoxaline derivatives in aquous media. Syn Commun 39:569–579Google Scholar
  74. 74.
    Liu JY, Liu J et al (2010) Efficient, ecofriendly, and practical process for the synthesis of quinoxalines catalyzed by amberlyst-15 in aqueous media. Synth Commun 40:2047–2056Google Scholar
  75. 75.
    Beheshtiha YS, Heravi MM et al (2010) Efficient and green synthesis of 1,2-disubstituted benzimidazoles and quinoxalines using brønsted acid ionic liquid, [(CH2) SO3HMIM][HSO4], in water at room temperature. Synth Commun 40:1216–1223Google Scholar
  76. 76.
    Krishnakumar B, Velmurugan R et al (2010) An efficient protocol for the green synthesis of quinoxaline and dipyridophenazine derivatives at room temperature using sulfated titania. Catal Commun 11:997–1002Google Scholar
  77. 77.
    Chavan HV, Adsul LK et al (2011) Polyethylene glycol in water: a simple, efficient and green protocol for the synthesis of quinoxalines. J Chem Sci 123:477–483Google Scholar
  78. 78.
    Kumbhar A, Kamble S et al (2012) Brönsted acid hydrotrope combined catalyst for environmentally benign synthesis of quinoxalines and pyrido[2,3-b]pyrazines in aqueous medium. Tetrahedron Lett 53:2756–2760Google Scholar
  79. 79.
    Kolvari E, Zolfigol MA et al (2012) Green synthesis of quinoxaline derivatives using p-dodecylbenzensulfonic acid as a surfactant-type Bronsted acid catalyst in water. Green Chem Lett Rev 5:155–159Google Scholar
  80. 80.
    Delpivo C, Micheletti G et al (2013) A green synthesis of quinoxalines and 2,3-dihydropyrazines. Synthesis 45:1546–1552Google Scholar
  81. 81.
    Kumar D, Seth K et al (2013) Surfactant micelles as microreactors for the synthesis of quinoxalines in water: scope and limitations of surfactant catalysis. RSC Adv 3:15157–15168Google Scholar
  82. 82.
    Bardajee GR (2013) ZrOCl2.8H2O in water: an efficient catalyst for rapid one-pot synthesis of pyridopyrazines, pyrazines and 2,3-disubstituted quinoxalines. Comptes Rendus Chimie 16:872–877Google Scholar
  83. 83.
    Madhav B, Murthy NS et al (2009) Biomimetic synthesis of quinoxalines in water. Tetrahedron Lett 50:6025–6028Google Scholar
  84. 84.
    Wan JP, Gan S-F (2009) Water mediated chemoselective synthesis of 1,2-disubstituted benzimidazoles using o-phenylenediamine and the extended synthesis of quinoxalines. Green Chem 11:1633–1637Google Scholar
  85. 85.
    Ghosh P, Mandal A (2012) Synthesis of functionalized benzimidazoles and quinoxalines catalyzed by sodium hexafluorophosphate bound Amberlite resin in aqueous medium. Tetrahedron Lett 53:6483–6488Google Scholar
  86. 86.
    Ghosh P, Mandal A et al (2013) Sodium dodecyl sulfate in water: greener approach for the synthesis of quinoxaline derivatives. Green Chem Lett Rev 6:45–54Google Scholar
  87. 87.
    Kumar BSPA, Madhav B et al (2011) Quinoxaline synthesis in novel tandem one-pot protocol. Tetrahedron Lett 52:2862–2865Google Scholar
  88. 88.
    Akkilagunta VK, Reddy VP et al (2010) Aqueous-phase aerobic oxidation of alcohols by ru/c in the presence of cyclodextrin: one-pot biomimetic approach to quinoxaline synthesis. Synlett 2571–2574Google Scholar
  89. 89.
    Bégué JP, Bonnet-Delpon D et al (2004) Fluorinated alcohols: new medium for selective and clean reaction. Synlett 1:18–29Google Scholar
  90. 90.
    Chebolu R, Kommi DN et al (2012) Hydrogen-bond driven electrophilic activation for selectivity control: the scope and limitations of fluorous alcohol promoted selective formation of 1,2-disubstituted benzimidazoles and mechanistic insight for rational of selectivity. J Org Chem 77:10158–10167Google Scholar
  91. 91.
    Khaksar S, Rostamnezhad F (2012) A novel one pot synthesis of quinoxaline derivatives in fluorinated alcohols. Bull Korean Chem Soc 33:2581–2585Google Scholar
  92. 92.
    Chen J, Spear SK et al (2005) Polyethylene glycol and solutions of polyethylene glycol as green reaction media. Green Chem 7:64–82Google Scholar
  93. 93.
    Chandrasekhar S, Reddy NK et al (2010) Oxidation of alkynes using PdCl2/CuCl2 in PEG as a recyclable catalytic system: one-pot synthesis of quinoxalines. Tetrahedron Lett 51:3623–3625Google Scholar
  94. 94.
    Cho CS, Ren WX et al (2007) Ketone as a new synthon for quinoxaline synthesis. Tetrahedron Lett 48:4665–4667Google Scholar
  95. 95.
    Wilkes JS (2002) A short history of ionic liquids—from molten salts to neoteric solvents. Green Chem 4:73–80Google Scholar
  96. 96.
    (a) Seddon KR (1997) Ionic liquids for clean technology. J Chem Tech Biotech 68:351–356. (b) Earle MJ, Seddon KR (2000) Ionic liquids. Green solvents for the future. Pure Appl Chem 72:1391–1398Google Scholar
  97. 97.
    Ranke J, Stolte S et at (2007) Design of sustainable chemical products: the example of ionic liquids. Chem Rev 107:2183–2206Google Scholar
  98. 98.
    Plechkova NV, Seddona KR (2008) Applications of ionic liquids in the chemical industry. Chem Soc Rev 37:123–150Google Scholar
  99. 99.
    Martins MA, Frizzo CP et al (2008) Ionic liquids in heterocyclic synthesis. Chem Rev 108:2015–2050Google Scholar
  100. 100.
    Hubbard CD, Illner P et al (2011) Understanding chemical reaction mechanisms in ionic liquids: successes and challenges. Chem Soc Rev 40:272–290Google Scholar
  101. 101.
    Aggarwal A, Lancaster NL et al (2002) The role of hydrogen bonding in controlling the selectivity of Diels–Alder reactions in room-temperature ionic liquids. Green Chem 4:517–520Google Scholar
  102. 102.
    (a) Sarkar A, Raha Roy S (2011) Non-solvent application of ionic liquids: organo-catalysis by 1-alkyl-3-methylimidazolium cation based room temperature ionic liquids for chemoselective N-tert-butyloxycarbonylation of amines and the influence of the C-2 hydrogen on catalytic efficiency. J Org Chem 76:7132–7140. (b) Sarkar A, Roy S et al (2011) Ionic liquid catalysed reaction of thiols with α,β-unsaturated carbonyl compounds- remarkable influence of the c-2 hydrogen and the anion. J Chem Soc Chem Commun 47:4538–4540. (c) Raha Roy S, Chakraborti AK (2010) Supramolecular Assemblies in Ionic Liquid catalysis for Aza-Michael Reaction. Org Lett 12:3866–3869. (d) Chakraborti AK, Raha Roy S (2009) On catalysis by ionic liquids. J Am Chem Soc 131:6902–6903. (e) Chakraborti AK, Raha Roy S et al (2008) Catalytic application of room temperature ionic liquids: [bmim][MeSO4] as a recyclable catalyst for synthesis of bis(indolyl)methanes. Ion-fishing by MALDI-TOF-TOF MS and MS/MS studies to probe the proposed mechanistic model of catalysis. Green Chem 10:1111–1118Google Scholar
  103. 103.
    Raha Roy S, Jadhavar PS et al (2011) Organo-catalytic application of room temperature ionic liquids: [bmim][meso4] as a recyclable organo-catalyst for one-pot multicomponent reaction for preparation of dihydropyrimidinones and –thiones. Synthesis 14:2261–2267.Google Scholar
  104. 104.
    Potewar TM, Ingale SA et al (2008) Efficient synthesis of quinoxalines in the ionic liquid 1-n-butylimidazolium tetrafluoroborate ([hbim]bf4) at ambient temperature. Synth Commun 38:3601–3612Google Scholar
  105. 105.
    Vahdat SM, Baghery SA (2013) Green and efficient protocol for the synthesis of quinoxaline, benzoxazole and benzimidazole derivatives using heteropolyanion-based ionic liquids: as a recyclable solid catalyst. Combi Chem High Throughput Screen 16:618–627Google Scholar
  106. 106.
    Li1 C, Guo T et al (2011) A green and efficient synthesis of quinoxaline derivatives catalyzed by 1-n-butyl-3-methylimmidazolium tetrafluoroborate. Bull Chem Soc Ethiop 25:455–460Google Scholar
  107. 107.
    Dong F, Kai G et al (2008) A practical and efficient synthesis of quinoxaline derivatives catalyzed by task-specific ionic liquid. Catal Commun 9:317–320Google Scholar
  108. 108.
    Zare A, Hasaninejad A et al (2010) Ionic liquid 1-butyl-3-methylimidazolium bromide ([bmim]Br): a green and neutral reaction media for the efficient, catalyst-free synthesis of quinoxaline derivatives. J Serb Chem Soc 75:1315–1324Google Scholar
  109. 109.
    Meshram HM, Ramesh P et al (2010) One-pot synthesis of quinoxaline-2-carboxylate derivatives using ionic liquid as reusable reaction media. Tetrahedron Lett 51:4313–4316Google Scholar
  110. 110.
    Zhang W, Berkeley W (2012) Green techniques for organic synthesis and medicinal chemistry. WileyGoogle Scholar
  111. 111.
    (a) Woodward JR, Jackson RJ et al (1997) Resonant radiofrequency magnetic field effects on a chemical reaction. Chem Phys Lett 272:376–382. (b) Kappe CO (2004) Controlled microwave heating in modern organic synthesis. Angew Chem Int Ed 43:6250–6284Google Scholar
  112. 112.
    (a) Motiwala HF, Kumar R et al (2007) Microwave-accelerated solvent- and catalyst-free synthesis of 4-aminoaryl/alkyl-7-chloroquinolines and 2-aminoaryl/alkylbenzothiazoles. Aust J Chem 60:369–374. (b) Kumar R, Selvam C et al (2005) Microwave-assisted direct synthesis of 2-substituted benzoxazoles from carboxylic acids under catalyst and solvent free conditions. Synlett 2005(9)1401–1404. (c) Chakraborti AK, Selvam C et al (2004) An efficient synthesis of benzothiazoles by direct condensation of carboxylic acids with 2-aminothiophenol under microwave irradiation. Synlett 851–855. (d) Chakraborti AK, Kaur G (1999) One-pot synthesis of nitriles from aldehydes under microwave irradiation: influence of the medium and mode of microwave irradiation on product formation. Tetrahedron 55:13265–13268Google Scholar
  113. 113.
    (a) Bougrin K, Loupy A et al (2005) Microwave assisted solvent free heterocyclic synthesis. J Photochem Photobiol C: Photochem Rev 6(2–3):139–167. (b) Daştan A, Aditya KA et al (2012) Environmentally benign synthesis of heterocyclic compounds by combined microwave-assisted heterogeneous catalytic approaches. Green Chem 14:17–37Google Scholar
  114. 114.
    Zhou FJ, Gong GX et al (2009) Microwave- assisted catalyst- free and solvent- free methods for the synthesis of quinoxalines. Synth Commun 39:3743–3754Google Scholar
  115. 115.
    Castellanos JJM, Hernández KR et al (2012) Microwave-assisted solvent-free synthesis and in vitro antibacterial screening of quinoxalines and pyrido[2,3b]pyrazines. Molecules 17:5164–5176Google Scholar
  116. 116.
    Zhou JF, Gong GX et al (2009) Catalyst-free and solvent-free method for the synthesis of quinoxalines under microwave irradiation. Chin Chem Lett 20:672–675Google Scholar
  117. 117.
    Zhao Z, Wisnoski DD et al (2004) General microwave- assisted protocols for the expedient synthesis of quinoxalines and heterocyclic pyrazines. Tetrahedron Lett 45:4873–4876Google Scholar
  118. 118.
    Mohsenzadeh F, Aghapoor K et al (2007) Benign approaches for the microwave-assisted synthesis of quinoxalines. J Braz Chem Soc 18:297–303Google Scholar
  119. 119.
    Zhang XZ, Wang J et al (2011) Microwave- assisted synthesis of quinoxalines in PEG-400. Synth Commun 41:2053–2063Google Scholar
  120. 120.
    Bandyopadhyay D, Mukherjee S et al (2010) An effective microwave-induced iodine-catalysed method for the synthesis of quinoxalines via condensation of 1,2-diamine with 1,2-dicarbonyl compounds. Molecules 15:4207–4212Google Scholar
  121. 121.
    Krishnakumar B, Velmurugan R et al (2010) An efficient protocol for the green synthesis of quinoxaline and dipyridophenazine derivatives at room temperature using sulfated titania. Catal Commun 11:997–1002Google Scholar
  122. 122.
    Aravind K, Ganesh A et al (2013) Microwave assisted synthesis, characterization and antibacterial activity of quinoxaline derivatives. J Chem Pharma Res 5:48–52Google Scholar
  123. 123.
    Fouad F (2013) Multistep soluble polymer-supported, microwave-assisted synthesis of quinoxalines. Green Chem Lett Rev 6:249–253Google Scholar
  124. 124.
    Ayaz M, Dietrich J et al (2011) A novel route to synthesize libraries of quinoxalines via Petasis methodology in two synthetic operations. Tetrahedron Lett 52:4821–4823Google Scholar
  125. 125.
    Kim SY, Park KH et al (2005) Manganese (1V) dioxide- catalyzed synthesis of quinoxalines under microwave irradiation. Chem Commun 14(10):1321–1323Google Scholar
  126. 126.
    (a) Comer E, Organ MG (2005) A microreactor for microwave-assisted capillary (continuous flow) organic synthesis. J Am Chem Soc 127:8160–8167. (b) Colombo M, Peretto I (2008) Chemistry strategies in early drug discovery: an overview of recent trends. Drug Disc Today 13:677–684Google Scholar
  127. 127.
    Bremner WS, Organ MG (2007) Multicomponent reactions to form heterocycles by microwave-assisted continuous flow organic synthesis. J Comb Chem 9:14–16Google Scholar
  128. 128.
    Martin LJ, Marzinzik AL (2011) Safe and reliable synthesis of diazoketones and quinoxalines in a continuous flow reactor. Org Lett 13:320–323Google Scholar

Copyright information

© Springer India 2014

Authors and Affiliations

  • Pradeep S. Jadhavar
    • 1
  • Dinesh Kumar
    • 1
  • Priyank Purohit
    • 1
  • Bhavin V. Pipaliya
    • 1
  • Asim Kumar
    • 1
  • Srikant Bhagat
    • 1
  • Asit K. Chakraborti
    • 1
    Email author
  1. 1.Department of Medicinal ChemistryNational Institute of Pharmaceutical Education and Research (NIPER)MohaliIndia

Personalised recommendations