Skip to main content
SpringerLink
Log in

An appropriate One-Pot Synthesis of a Series of 7,7-Dimethyl-10-aryl-7,8-dihydro-5H-indeno[1,2-b]quinoline-9,11(6H,10H)-diones Using Tribromomelamine as an Efficient Organocatalyst

  • Research Paper
  • Published:
Iranian Journal of Science and Technology, Transactions A: Science Aims and scope Submit manuscript

Abstract

A mild and efficient protocol for the synthesis of 7,7-dimethyl-10-aryl-7,8-dihydro-5H-indeno[1,2-b]quinoline-9,11(6H,10H)-diones via a one-pot four component condensation of aromatic aldehydes, 1,3-indandione, dimedone and ammonium acetate using tribromomelamine (TBM) as a catalyst is described. The reaction occurs in ethanol to give the corresponding products in good to high yields in short times. The effect of various solvent and catalyst amount was investigated. The results of the presented protocol in comparison with the different available catalysts show that TBM presented better results. A possible mechanism for the formation of indeno[1,2-b]quinolines using TBM as a catalyst has been proposed. The salient features of the present method are: high yields, mild reaction conditions, simple and straightforward work-up, cost-effective and environmentally benign procedure.

This is a preview of subscription content, log in via an institution to check access.

Access this article

Log in via an institution

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

Institutional subscriptions

Scheme 1
Fig. 1
Scheme 2

Similar content being viewed by others

References

  • Abaszadeh M, Seifi M, Ghashang M (2015) Multi-component preparation of diethyl/methyl 1,3-diaryl-1,2,3,6-tetrahydropyrimidine-4,5-dicarboxylates using hydrated phosphomolybdic acid as an efficient catalyst. Iran J Catal 5:113–117

    Google Scholar 

  • Ali MM, Tasneem KC, Rajanna KC, Prakash PKS (2001) A facile and selective procedure for transesterification of β-keto esters promoted by Yttria-Zirconia based Lewis acid catalyst. Synlett 2000:251–253

    Article  Google Scholar 

  • Aswin K, Ghashang M, Mansoor SS (2015) An efficient synthesis of 4-aryl-7-benzylidene-hexahydro-2H-cyclopenta[d] pyrimidin-2-ones/thiones catalyzed by p-dodecyl benzene sulfonic acid. Iran J Catal 5:175–182

    Google Scholar 

  • Baraznenok IL, Nenajdenko VG, Balenkova ES (1999) 3-Trifloxy-3-trifluoro methyl propeniminium triflate: reaction with aromatic amines—an efficient synthesis of 2-trifluoromethylquinolines. Eur J Org Chem 1999:937–941

    Article  Google Scholar 

  • Chakrabarty S, Croft MS, Marko MG, Moyna G (2013) Synthesis and evaluation as potential anticancer agents of novel tetracyclic indenoquinoline derivatives. Bioorg Med Chem 21:1143–1149

    Article  Google Scholar 

  • Chen YL, Hung HM, Lu CM, Li KC, Tzeng CC (2004) Synthesis and anticancer evaluation of certain indolo[2,3-b]quinoline derivatives. Bioorg Med Chem 12:6539–6546

    Article  Google Scholar 

  • Cho CS, Kim BT, Kim TJ, Shim SC (2001) Ruthenium catalyzed oxidative cyclisation of 2-amino benzyl alcohol with ketones: modified Friedlaender quinolone synthesis. Chem Commun 24:2576–2577

    Article  Google Scholar 

  • Crousse B, Begue JP, Bonnet-Delpon DJ (2000) Synthesis of 2-CF3-tetrahydro quinoline and quinoline derivatives from CF3-N-aryl-aldimine. J Org Chem 65:5009–5013

    Article  Google Scholar 

  • Damavandi S, Sandaroos R (2011) Solvent-free one pot synthesis of indenoquinolinones catalyzed by iron(III) triflate. Heterocycl Commun 17:121–124

    Google Scholar 

  • Davoodi E, Youseftabar-Miri L, Hosseinjani-Pirdehi H (2014) l-proline: an efficient catalyst for the synthesis of quinoline derivatives in aqueous media. Iran J Catal 4:99–104

    Google Scholar 

  • Domling A, Ugi I (2000) Multicomponent reactions with isocyanides. Angew Chem Int Ed 39:3168–3210

    Article  Google Scholar 

  • Eswaran S, Adhikari AV, Chowdhury IH, Pal NK, Thomas KD (2010) New quinoline derivatives: synthesis and investigation of antibacterial and anti-tuberculosis properties. Eur J Med Chem 45:3374–3383

    Article  Google Scholar 

  • Ghashang M, Mansoor SS, Aswin K (2014a) Thiourea dioxide: an efficient and reusable organocatalyst for the rapid one-pot synthesis of pyrano[4,3-b]pyran derivatives in water. Chin J Catal 35:127–133

    Article  Google Scholar 

  • Ghashang M, Mansoor SS, Aswin K (2014b) Poly(4-vinylpyridinium)hydrogen sulfate: a novel and efficient catalyst for the synthesis of 13-aryl-indeno[1,2-b]naphtha[1,2-e]pyran-12(13H)-ones under solvent-free conditions. Chin J Catal 35:43–48

    Article  Google Scholar 

  • Ghashang M, Mansoor SS, Shafiee MRM, Kargar M, Biregan MN, Azimi F, Taghrir H (2016) Green chemistry preparation of MgO nano powders: efficient catalyst for the synthesis of thiochromeno[4,3-b]pyran and thiopyrano[4,3-b]pyran derivatives. J Sulf Chem 37:377–390

    Article  Google Scholar 

  • Ghorbani-Choghamarani A, Rashidimoghadam R (2014) One-pot synthesis of 1-amidoalkyl-2-naphthols catalyzed by melamine-Br3 under solvent-free conditions. Chin J Catal 35:1024–1029

    Article  Google Scholar 

  • Ghorbani-Choghamarani A, Zolfigol MA, Hajjami H, Jafari S (2008) Trimethyl silylation of hydroxyl group with 1,1,1,3,3,3-hexamethyldisilazane (HMDS) catalyzed by tribromomelamine (TBM). J Chin Chem Soc 55:1208–1213

    Article  Google Scholar 

  • Hajjami M, Ghorbani-Choghamarani A, Karamshahi Z, Norouzi M (2014) Tribromo melamine as novel and versatile catalyst for the formylation and acetylation of alcohols. Chin J Catal 35:260–263

    Article  Google Scholar 

  • Hazeri N, Mohamadian-Souri S, Maghsoodlou MT, Lashkari M, Ghashang M (2015) A facile one-pot four-component synthesis of dihydropyrrol-2-ones using Cl3CCOOH. Iran J Catal 5:9–14

    Google Scholar 

  • Heravi MM, Hosseini T, Derikvand F, Beheshtiha SYS, Bamoharram FF (2010) H6P2W18O62·18H2O—Catalyzed, three-component, one-pot synthesis of indeno[1,2-b]quinoline-7-one derivatives. Synth Commun 40:2402–2406

    Article  Google Scholar 

  • Iranpoor N, Firouzabadi H, Nowrouzi N, Khalili D (2009) Selective mono- and di-N-alkylation of aromatic amines with alcohols and acylation of aromatic amines using Ph3P/DDQ. Tetrahedron 65:3893–3899

    Article  Google Scholar 

  • Khaligh NG (2014) Three-component, one-pot synthesis of benzo[f]indenoquinoline derivatives catalyzed by poly(4-vinylpyridinium) hydrogen sulfate. Chin J Catal 35:474–480

    Article  Google Scholar 

  • Khaligh NG (2015) 3-Methyl-1-sulfonic acid imidazolium hydrogen sulfate-catalyzed three-component, one-pot synthesis of 13-aryl-12H-benzo[f]indeno[1,2-b]quinoline-12-one derivatives. Res Chem Intermed 41:5411–5421

    Article  Google Scholar 

  • Khaligh NG, Mihankhah T (2015) Poly(4-vinylpyridinium) hydrogen sulfate catalyzed synthesis of 12-aryl-12-hydro-5H-benzo[g]indeno[2,1-b]quinoline-6,11,13-trione derivatives. Res Chem Intermed 41:4569–4579

    Article  Google Scholar 

  • Khazaei A, Zolfigol MA, Moosavi-Zare AR, Zare A, Khojasteh M, Asgari Z, Khakyzadeh V, Khalafi- Nezhad A (2012) Organocatalyst trityl chloride efficiently promoted the solvent-free synthesis of 12-aryl-8,9,10,12-tetrahydrobenzo[a]-xanthen-11-ones by in situ formation of carbocationic system in neutral media. Catal Commun 20:54–57

    Article  Google Scholar 

  • Khazaei A, Zolfigol MA, Moosavi-Zare AR, Abi F, Zare A, Kaveh H, Khakyzadeh V, Kazem-Rostami M, Parhami A, Torabi-Monfared H (2013) Discovery of an in situ carbocationic system using trityl chloride as a homogeneous organocatalyst for the solvent-free condensation of β-naphthol with aldehydes and amides/thioamides/alkyl carbamates in neutral media. Tetrahedron 69:212–218

    Article  Google Scholar 

  • Kiyani H, Ghorbani F (2015) Potassium phthalimide: an efficient and simple organocatalyst for the one-pot synthesis of dihydropyrano[3,2-c]chromenes in aqueous media. Res Chem Intermed 41:4031–4046

    Article  Google Scholar 

  • Lin XF, Cui SL, Wang YG (2006) A highly efficient synthesis of 1,2,3,4-tetrahydroquinolines by molecular iodine-catalyzed domino reaction of anilines with cyclic enol ethers. Tetrahedron Lett 47:4509–4512

    Article  Google Scholar 

  • Mamaghani M, Larghani TH (2012) Ultrasound promoted one-pot three-component synthesis of novel 7-aryl-8H-benzo[h]indeno[1,2-b]quinolin-8-ones under solvent-free conditions. J Chem Res 36:235–237

    Article  Google Scholar 

  • Mansoor SS, Ghashang M, Aswin K (2015) Facile one-pot synthesis of a novel series of 7-aryl-8H-benzo[h]indeno[1,2-b]quinoline-8-one derivatives catalyzed by tribromo melamine. Res Chem Intermed 41:6907–6926

    Article  Google Scholar 

  • Meshram HM, Reddy GS, Reddy MM, Yadav JS (1998) Zinc mediated facile amide formation: application to alkyl, aryl, heterocycle, carbohydrate and amino acids. Tetrahedron Lett 39:4103–4106

    Article  Google Scholar 

  • Motamedi-Asl A, Khandan-Barani K (2015) Lactic acid as an efficient catalyst for the one-pot three-component synthesis of 1-amidoalkyl-2-naphthols under thermal solvent-free conditions. Iran J Catal 5:339–343

    Google Scholar 

  • Palacios F, de Retana AMO, Oyarzabal J (1999) A simple synthesis of 3-phosphonyl-4-aminoquinolines from β-enaminophosphonates. Tetrahedron 55:5947–5964

    Article  Google Scholar 

  • Sakata G, Makino K, Karasawa Y (1988) Recent progress in the quinoline chemistry. Synthesis and biological activity. Heterocycles 27:2481–2515

    Article  Google Scholar 

  • Sandaroos R, Vadi M, Damavandi S (2013) Efficient example of cross-linked polymeric catalysed synthesis of 7H-benzo[h]indeno[1,2-b]quinolin-8-one and 8H-naphtho[2,3-h]indeno[1,2-b]quinolin-9-one. J Chem Sci 125:1497–1501

    Article  Google Scholar 

  • Shirini F, Beigbaghlou SS, Atghia SV, Mousazadeh SAR (2013) Multi-component one-pot synthesis of unsymmetrical dihydro-5H-indeno[1,2-b]quinolines as new pH indicators. Dyes Pigm 97:19–25

    Article  Google Scholar 

  • Tseng CH, Chen YL, Lu PJ, Yangd CN, Tzeng CC (2008) Synthesis and antiproliferative evaluation of certain indeno[1,2-c]quinoline derivatives. Bioorg Med Chem 16:3153–3162

    Article  Google Scholar 

  • Tu SJ, Jiang B, Jia RH, Zhang JY, Zhang Y, Yao CS, Shi F (2006) An efficient one-pot, three-component synthesis of indeno[1,2-b]quinoline-9,11(6H,10H)-dione, acridine-1,8(2H,5H)-dione and quinoline-3-carbonitrile derivatives from enaminones. J Org Biomol Chem 4:3664–3668

    Article  Google Scholar 

  • Tu SJ, Wu SS, Yan S, Hao WJ, Zhang XH, Cao XD, Han ZG, Jiang B, Shi F, Xia M, Zhou JF (2009) Design and microwave-assisted synthesis of naphtho[2,3-f]quinoline derivatives and their luminescent properties. J Comb Chem 11:239–242

    Article  Google Scholar 

  • Upadhayaya RS, Jaya Kishore V, Nageswara Rao V, Sharma V, Dixit SS, Chattopadhyaya J (2009a) Design, synthesis, biological evaluation and molecular modelling studies of novel quinoline derivatives against Mycobacterium tuberculosis. Bioorg Med Chem 17:2830–2841

    Article  Google Scholar 

  • Upadhayaya RS, Kulkarni GM, Jaya Kishore V, Nageswara Rao V, Sharma V, Dixit SS, Chattopadhyaya J (2009b) Design, synthesis and biological evaluation of novel triazole, urea and thiourea derivatives of quinoline against Mycobacterium tuberculosis. Bioorg Med Chem 17:4681–4692

    Article  Google Scholar 

  • Upadhayaya RS, Jaya Kishore V, Kardile RA, Lahore SV, Dixit SS, Deokar HS, Shinde PD, Chattopadhyaya J (2010a) Novel quinoline and naphthalene derivatives as potent antimycobacterial agents. Eur J Med Chem 45:1854–1867

    Article  Google Scholar 

  • Upadhayaya RS, Lahore SV, Sayyed AY, Dixit SS, Shinde PD, Chattopadhyaya J (2010b) Conformationally-constrained indeno[2,1-c]quinolines—a new class of anti-mycobacterial agents. Org Biomol Chem 8:2180–2197

    Article  Google Scholar 

  • Upadhayaya RS, Shinde PD, Sayyed AY, Kadam SA, Bawane AN, Poddar A, Plashkevych O, Földesi A, Chattopadhyaya J (2010c) Synthesis and structure of azole-fused indeno[2,1-c]quinolines and their anti-mycobacterial properties. Org Biomol Chem 8:5661–5673

    Article  Google Scholar 

  • Upadhayaya RS, Shinde PD, Kadam SA, Bawane AN, Sayyed AY, Kardile RA, Gitay PN, Lahore SV, Dixit SS, Földesi A, Chattopadhyaya J (2011) Synthesis and anti-mycobacterial activity of prodrugs of indeno[2,1-c]quinoline derivatives. Euro J Med Chem 46:1306–1324

    Article  Google Scholar 

  • Verma S, Kumar S, Jain SL, Sain B (2011) Thiourea dioxide promoted efficient organocatalytic one-pot synthesis of a library of novel heterocyclic compounds. Org Biomol Chem 9:6943–6948

    Article  Google Scholar 

  • Wang XS, Zhang MM, Zeng ZS, Shi DQ, Tu SJ, Wei XY, Zong ZM (2006) A clean synthesis of polyhydroacridine and indenoquinoline derivatives catalyzed by triethylbenzylammonium chloride in aqueous media. J Heterocycl Chem 43:989–996

    Article  Google Scholar 

  • Wu LQ (2012) Tribromomelamine: a novel and efficient catalyst for the synthesis 2-arylthiazolines under solvent-free conditions. E-J Chem 9:1035–1041

    Article  Google Scholar 

  • Zare A, Merajoddin M, Zolfigol MA (2013) Study of an in situ carbocationic system formed from trityl chloride (Ph3CCl) as an efficient organocatalyst for the condensation of dimedone with arylaldehydes. Iran J Catal 3:83–90

    Google Scholar 

  • Zolfigol MA, Baghery S, Moosavi-Zare AR, Vahdat SM, Alinezhadd H, Norouzid M (2014) Synthesis of the first nano ionic liquid 1-methylimidazolium trinitromethanide [HMIM]C(NO2)3 and its catalytic use for Hanztsch four-component condensation. RSC Adv 4:57662–57670

    Article  Google Scholar 

Download references

Acknowledgements

The work was supported by C. Abdul Hakeem College, Melvisharam, India.

Author information

Authors and Affiliations

  1. Bioactive Organic Molecule Synthetic Unit, Research Department of Chemistry, C. Abdul Hakeem College (Autonomous), Melvisharam, 632 509, Tamil Nadu, India

    Prasanna Nithiya Sudhan & Syed Sheik Mansoor

  2. Department of Chemistry, Faculty of Sciences, Najafabad Branch, Islamic Azad University, Najafabad, Esfahan, Iran

    Majid Ghashang

Authors
  1. Prasanna Nithiya Sudhan
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Majid Ghashang
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. Syed Sheik Mansoor
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to Syed Sheik Mansoor.

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Sudhan, P.N., Ghashang, M. & Mansoor, S.S. An appropriate One-Pot Synthesis of a Series of 7,7-Dimethyl-10-aryl-7,8-dihydro-5H-indeno[1,2-b]quinoline-9,11(6H,10H)-diones Using Tribromomelamine as an Efficient Organocatalyst. Iran J Sci Technol Trans Sci 42, 1895–1904 (2018). https://doi.org/10.1007/s40995-017-0447-y

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s40995-017-0447-y

Keywords

Search

Navigation