Skip to main content
SpringerLink
Log in

Synthesis of New Cyano-Quinoline Derivatives by the Baylis–Hillman Reaction

  • Original Paper
  • Published:
Journal of Chemical Crystallography Aims and scope Submit manuscript

Abstract

Quinoline derivatives represent the major class of heterocycles, and a number of preparations have been known since the late 1800s. The quinoline ring system occurs in various natural products, especially in alkaloids. The quinoline skeleton is often used for the design of many synthetic compounds with diverse pharmacological properties. A new quinoline derivative was crystallized from the reaction between acrylonitrile and 2-chloro-3-formyl quinoline derivatives which had themselves been prepared from the Meth Cohn method. The reaction catalyzed by DABCO, gives rise to five new 2-[2-Chloro-quinolin-3-yl)-hydroxy-methyl]-acrylonitrile derivatives. The crystal structure of the 7-Methyoxy-substituted one crystallizes in monoclinic space group C2/c, a = 17.1090 (7) Å, b = 8.3119 (5) Å, c = 19.7949 (6) Å, β = 101.922 (2)°, and its cohesion was assured by O–H···N, O–H···O and C–H···O hydrogen bonds.

Graphical Abstract

The aim of this paper is to discuss the synthesis strategy of new cyano-quinoline derivatives, the interpretation of the crystallographic and spectroscopic results, the structural study and to the hydrogen bonds assuring the molecular cohesion within the crystals.

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

Fig. 1
Fig. 2
Fig. 3
Fig. 4
Fig. 5
Fig. 6

Similar content being viewed by others

References

  1. Michael JP (1997) Nat Prod Rep 14:605

    Article  CAS  Google Scholar 

  2. Balasubramanian M, Keay JG (1996) In: Katritzky AR, Rees CW, Scriven EFV (eds) Comprehensive heterocyclic chemistry II, vol 5. Pergamon Press, Oxford, pp 245–300

    Chapter  Google Scholar 

  3. Yates FS (1984) In: Katritzky AR, Rees CW (eds) Comprehensive hetercyclic chemistry, vol 2. Pergamon Press, Oxford, p 511

    Chapter  Google Scholar 

  4. Levy S, Azoulay SJ (1994) Cardiovas. Electrophysiol. 5:635–636

    Article  CAS  Google Scholar 

  5. Wenckebach KF (1923) JAMA 81:472–474

    Article  Google Scholar 

  6. Lutz RE, Bailey PS, Clark MT, Codington JF, Dinet AJ, Freek JA, Harnest GH, Leak NH, Martin TA, Rowlett RJ, Salisbury JM, Shearer NH, Smith JD, Wilson JW (1946) J Am Chem Soc 68:1813

    Article  Google Scholar 

  7. Surrey AE, Hammer HF (1950) J Am Chem Soc 72:1814

    Article  CAS  Google Scholar 

  8. Burckhalter JH, Brinigar WS, Thompson PS (1961) J Org Chem 26:4070

    Article  CAS  Google Scholar 

  9. Bilker O, Lindo V, Panico M, Etiene AE, Paxton T, Dell A, Rogers M, Sinden RE, Morris HR (1998) Nature 392:289–292

    Article  Google Scholar 

  10. Roma G, Braccio MD, Grossi G, Mattioli F, Ghia H (2000) Eur J Med Chem 35:1021–1035

    Article  CAS  Google Scholar 

  11. Chen Y-L, Fang K-C, Sheu J-Y, Hsu S-L, Tzeng C-C (2000) J Med Chem 44:2374–2377

    Article  Google Scholar 

  12. Winstanley PA (2000) Parasitol Today 16:146–153

    Article  CAS  Google Scholar 

  13. Desai PK, Desai P, Machhi D, Desai CM, Patel D (1996) J Indian Chem Sect B 35:871

    Google Scholar 

  14. Fang K-C, Chen Y-L, Sheu J-Y, Wang T-C, Tzeng C-C (2000) J Med Chem 43:3809–3812

    Article  CAS  Google Scholar 

  15. Chevalier J, Atifi S, Eyraud A, Mahamoud A, Barbe J, Pages J–M (2001) J Med Chem 44:4023–4026

    Article  CAS  Google Scholar 

  16. Phan LT, Jian T, Chen Z, Qiu Y-L, Wang Z, Beach T, Polemeropoulos A, Or YS (2004) J Med Chem 47:2965–2968

    Article  CAS  Google Scholar 

  17. Benkovic SJ, Baker SJ, Alley MRK, Woo Y-H, Zhang Y-K, Akama T, Mao W, Baboval J, Rajagopalan PTR, Wall M, Kahng LS, Tavassoli A, Shapiro L (2005) J Med Chem 48:7468–7476

    Article  CAS  Google Scholar 

  18. Majerz-Maniecka K, Oleksyn B, Musiol R, Podeszwa B, Polanski J (2005) Joint meeting on medicinal chemistry. Vienna, Austria, June 20–23. Sci Pharm 73 (Suppl. 1):194

    Google Scholar 

  19. Vargas LY, Castelli MV, Kouznetsov VV, Urbina JM, Lopez SN, Sortino M, Enriz RD, Ribas JC, Zacchino S (2003) Bioorg Med Chem 11:1531–1550

    Article  Google Scholar 

  20. Singh M, Singh MP, Ablordeppey SY (1996) Drug Dev Ind Pharm 22:377–381

    Article  CAS  Google Scholar 

  21. Wilson WD, Zhao M, Patterson SE, Wydra RL, Janda L, Strekowski L (1992) Med Chem Res 2:102

    CAS  Google Scholar 

  22. Strekowski L, Mokrosz JL, Honkan VA, Czarny A, Cegla MT, Wydra RL, Patterson SE, Schinazi RF (1991) J Med Chem 34:1739

    Article  CAS  Google Scholar 

  23. Atwell GJ, Baguley BC, Denny WA (1989) J Med Chem 32:393

    Article  Google Scholar 

  24. Dassonneville L, Lansiaux A, Wattelet A, Wattez N, Mahieu C, Van Miert S, Pieters L, Bailly C (2000) Eur J Pharmacol 409:9–18

    Article  CAS  Google Scholar 

  25. Dassonneville L, Bonjean K, De Pauw-Gillet M-C, Colson P, Houssier C, Quetin-Leclercq J, Angenot L, Ablordeppey SY (2002) Bioorg Med Chem 10:1337–1346

    Article  Google Scholar 

  26. Bailly C (1999) Biochemistry 38:7719–7726

    Article  Google Scholar 

  27. Bailly C, Laine W, Baldeyrou B, De Pauw-Gillet M-C, Colson P, Houssier C, Cimanga K, Miert SV, Vlietinck AJ, Pieters L (2000) Anti-Cancer Drug Des 15:191–201

    CAS  Google Scholar 

  28. Khan MTH (2007) Quinoline analogs as antiangiogenic agents and telomerase inhibitors. In: Khan MTH, Gupta R (eds) Bioactive heterocycles V. R. Springer-Verlag, Berlin. Top Heterocycl Chem 11:213–229 and references cited therein

  29. Cheng X-M, Lee C, Klutchko S, Winters T, Reynolds EE, Welch KM, Flynn MA, Doherty AM (1996) Bioorg Med Chem 6:2999

    Article  CAS  Google Scholar 

  30. Anzini M, Cappelli A, Vomero S, Giorgi G, Langer T, Hamon M, Merahi N, Emerit BM, Cagnotto A, Skorupska M, Mennini T, Pinto JC (1995) J Med Chem 38:2692

    Article  CAS  Google Scholar 

  31. Giardina GAM, Sarau HM, Farina C, Medhurst AD, Grugni M, Raveglia LF, Schmidt DB, Rigolio R, Luttmann M, Vecchietti V, Hay DWP (1997) J Med Chem 50:1794

    Google Scholar 

  32. Van Inwegan RG, Khandwala A, Gordon R, Sonnino P, Coutts S, Jolly S (1987) J Pharmacol Exp Ther 24:117

    Google Scholar 

  33. Gauthier JY, Jones T, Champion E, Charette L, Dehaven R, Ford-Hutchinson AW, Hoogsteen K, Lord A, Masson P, Piechuta H, Pong SS, Springer JP, Therien M, Zamboni R, Young RN (1990) J Med Chem 33:2841

    Article  CAS  Google Scholar 

  34. Maguire MP, Sheets KR, McVety K, Spada AP, Zilberstein A (1994) J Med Chem 37:2129

    Article  CAS  Google Scholar 

  35. Ife RJ, Brown TH, Keeling DJ, Leach CA, Meeson ML, Parsons ME, Reavill DR, Theobald CJ, Wiggall K (1992) J Med Chem 35:3413

    Article  CAS  Google Scholar 

  36. Chen S-F, Papp LM, Ardecky RJ, Rao GV, Hesson DP, Forbes M, Desxter DL (1990) Biochem Pharmacol 40:709

    Article  CAS  Google Scholar 

  37. Zeevi A, Yao G-Z, Venkataramanan R, Duqesnoy RJ, Todo S, Fung JJ, Starzl TE (1993) Transpl Proc 25:781

    CAS  Google Scholar 

  38. Musser JH, Chakraborty UR, Sciortino S, Gordon RJ, Khandawala A, Neiss ES, Pruss TP, Van Inwegen R, Weinryb I, Coutts SM (1987) J Med Chem 30:96

    Article  CAS  Google Scholar 

  39. Jones G (1996) In: Katritzky AR, Rees CW, Scriven EFV (eds) Comprehensive heterocyclic chemistry II, vol 5. Pergamon Press, Oxford, pp 167–243 and references cited therein

  40. Holla BS, Mahalinga M, Karthikeyan MS, Akberalib PM, Shettyc NS (2006) Bioorg Med Chem 14:2040–2047

    Article  CAS  Google Scholar 

  41. Fishbein L (1979) Potential industrial carcinogens and mutagens. Elsevier Scientific Publishing Company, Amsterdam, pp 417–419

    Google Scholar 

  42. Smirnov RF, Tikhomirov BI, Marinchenko GV, Yakubchik AI (1973) Polym Sci U.S.S.R. 15:832–841

    Article  Google Scholar 

  43. Całus S, Gondek E, Danel A, Jarosz B, Pokładko M, Kityk AV (2007) Mater Lett 61:3292–3295

    Article  Google Scholar 

  44. Caeiro G, Lopes JM, Magnoux P, Ayrault P, Ribeiro FR (2007) J Catal 249:234–243

    Article  CAS  Google Scholar 

  45. Drewes SE, Roos GHP (1988) Tetrahedron 44:4653

    Article  CAS  Google Scholar 

  46. Basavaiah D, Dharma Rao P, Suguna Hy (1996) Tetrahedron 52:8001

    Article  CAS  Google Scholar 

  47. Ciganek E (1997) Org React 51:201

    CAS  Google Scholar 

  48. Basavaiah D, Jaganmohan Rao A, Satyanarayana T (2003) Chem Rev 103:811

    Article  CAS  Google Scholar 

  49. Baylis AB, Hillman MED (1972) German patent, 21155113. Chem Abstr 77:34174

  50. Meth Cohn O, Narine B, Tarnowski B (1981) J Chem Soc Perkin Trans 1:1520–1530

    Article  Google Scholar 

  51. Narender P, Srinivas U, Gangadasu B, Biswas S, Jayathirtha Rao V (2005) Bioorganic Medicinal Chem Lett 15:5378–5381

    Article  CAS  Google Scholar 

  52. Oxford Diffraction (2005) Xcalibur CCD system, CrysAlis Software system, Version 1.171. Oxford Diffraction Ltd., Abington

  53. Farrugia LJ (1999) J Appl Crystallogr 32:837–838

    Article  CAS  Google Scholar 

  54. Burla MC, Caliandro R, Camalli M, Carrozzini B, Cascarano GL, De Caro L, Giacovazzo C, Polidori G, Spagna R (2005) J Appl Crystallogr 38:381–388

    Article  CAS  Google Scholar 

  55. Sheldrick GM (1997) SHELXL97. University of Göttingen, Germany

    Google Scholar 

  56. Nardellli M (1999) J Appl Crystallogr 32:563–571

    Article  Google Scholar 

  57. Farrugia LJ (1997) J Appl Crystallogr 30:565

    Article  CAS  Google Scholar 

  58. Bruno IJ, Cole JC, Edgington PR, Kessler M, Macrae CF, McCabe P, Pearson J, Taylor R (2002) Acta Cryst. B58:389–397

    CAS  Google Scholar 

  59. Spek AL (2003) J Appl Crystallogr 36:7–13

    Article  CAS  Google Scholar 

  60. Kalkhambkar RG, Kulkarni GM, Hwang W-S, Lee C-S (2008) Acta Cryst E64:o258

    CAS  Google Scholar 

  61. Benzerka S, Bouraiou A, Bouacida S, Debache A, Belfaitah A (2008) Acta Cryst E64:o2115–o2116

    CAS  Google Scholar 

  62. Insuasty B, Torres H, Cobo J, Lowd JN, Glidewell C (2006) Acta Cryst C62:o39–o41

    CAS  Google Scholar 

  63. Jasinski JP, Butcher RJ, Mayekar AN, Yathirajan HS, Narayana B, Sarojini BK (2010) J. Mol. Struc. 980:172–181

    Article  CAS  Google Scholar 

  64. Roopan SM, Khan FN, Kumar AS, Hathwar VR, Akkurt M (2010) Acta Cryst E66:o1542

    CAS  Google Scholar 

  65. Roopan SM, Khan FN, Kumar R, Hathwar VR, Akkurt M (2010) Acta Cryst E66:o1543

    CAS  Google Scholar 

  66. Khan FN, Roopan SM, Hathwar VR, Ng SW (2010) Acta Cryst E66:o201

    CAS  Google Scholar 

  67. Khan FN, Roopan SM, Kushwaha AK, Hathwar VR, Akkurt M (2010) Acta Cryst E66:o1544

    CAS  Google Scholar 

  68. Khan FN, Roopan SM, Hathwar VR, Rajesh R, Rauf MK (2010) Acta Cryst E66:o953

    CAS  Google Scholar 

  69. Khan FN, Roopan M, Hathwar VR, Ng SW (2010) Acta Cryst E66:o200

    CAS  Google Scholar 

  70. Bernstein J, Davis RE, Shimoni L, Chang N-L (1995) Angew Chem Int Ed Engl 34:1555–1573

    Article  CAS  Google Scholar 

  71. Williams DH, Fleming I (1966) Spectroscopic methods in organic chemistry. McGraw-Hill, New York

    Google Scholar 

  72. Silverstein RM, Bassler GC, Morrill TC (1991) Spectrometric identification of organic compounds. Wiley, New York

    Google Scholar 

Download references

Acknowledgments

The authors acknowledge Dr S. Triki from ‘’Laboratoire de Chimie, Electrochimie Moléculaires et Chimie Analytique’’, équipe des ‘’Matériaux moléculaires et des systèmes organisés électroactifs’’ (UMR CNRS 6521-Université de Bretagne Occidentale, Brest, France) for providing diffraction facilities and ‘’le Centre Universitaire de Khenchela’’ for financial support. M.L thanks Paul MORSET for rich discussions.

Author information

Authors and Affiliations

  1. Département de Chimie, Faculté des Sciences, Université ‘’Hadj Lakhdar’’, Batna, 05000, Algérie

    Fatiha Guenfoud & Mohammed Laabassi

  2. Laboratoire des Structures, Propriétés et Interactions Interatomiques LASPI2A, Institut des Sciences et Technologie, Université ‘’Abbes Laghrour’’, Khenchela, 40000, Algérie

    Amani Direm & Nourredine Benali-Cherif

Authors
  1. Fatiha Guenfoud
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Amani Direm
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. Mohammed Laabassi
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. Nourredine Benali-Cherif
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to Amani Direm.

Rights and permissions

Reprints and permissions

About this article

Cite this article

Guenfoud, F., Direm, A., Laabassi, M. et al. Synthesis of New Cyano-Quinoline Derivatives by the Baylis–Hillman Reaction. J Chem Crystallogr 42, 989–996 (2012). https://doi.org/10.1007/s10870-012-0325-6

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s10870-012-0325-6

Keywords

Search

Navigation