Skip to main content
SpringerLink
Log in

Organocatalyzed domino reactions: diversity oriented synthesis of pyran-annulated scaffolds using in situ-developed benzylidenemalononitriles

  • Published:
Research on Chemical Intermediates Aims and scope Submit manuscript

Abstract

Molecular diversity for the synthesis of pyran annulated heterocyclic scaffolds has been achieved from the multicomponent reaction of aldehyde, malonitrile and a third participant such as dimedone, barbituric acid and 3-methyl-1H-pyrazol-5(4H)-one. The reactions completed successfully using in situ-developed benzylidenemalononitriles via Knoevenagel reaction catalyzed by aspartic acid as a new efficient organo-catalyst in aqueous ethanol as a green medium at ambient conditions.

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
Scheme 1
Scheme 2
Scheme 3
Scheme 4
Scheme 5

Similar content being viewed by others

References

  1. G. Feuer, in Progress in Medicinal Chemistry, ed. by G.P. Ellis, G.P. West (North-Holland Publishing Company, New York, 1974), p. 85

    Google Scholar 

  2. F.M. Dean, Naturally Occurring Oxygen Containing Compounds (Butterworth-Heinemann, London, 1963), pp. 176–220

    Google Scholar 

  3. A. Goel, V.J. Ram, Tetrahedron 65, 7865 (2009)

    Article  CAS  Google Scholar 

  4. L. Bonsignore, G. Loy, D. Secci, A. Calignano, Eur. J. Med. Chem. 28, 517 (1993)

    Article  CAS  Google Scholar 

  5. J.Y.C. Wu, W.F. Fong, J.X. Zhang, C.H. Leung, H.L. Kwong, M.S. Yang, D. Li, H.Y. Cheung, Eur. J. Pharmacol. 473, 9 (2003)

    Article  CAS  Google Scholar 

  6. G.M. Cingolani, F. Gualtteri, M. Pigin, J. Med. Chem. 12, 531 (1961)

    Article  Google Scholar 

  7. D.O. Moon, K.C. Kim, C.Y. Jin, M.H. Han, C. Park, K.J. Lee, Y.M. Park, Y.H. Choi, G.Y. Kim, Int. Immunopharmacol. 7, 222 (2007)

    Article  CAS  Google Scholar 

  8. L.R. Morgan, B.S. Jursic, C.L. Hooper, D.M. Neumann, K. Thangaraj, B. Leblance, Bioorg. Med. Chem. Lett. 12, 3407 (2002)

    Article  CAS  Google Scholar 

  9. M. Rueping, E. Sugiono, E. Merino, Chem. Eur. J. 14, 6329 (2008)

    Article  CAS  Google Scholar 

  10. P.S. Elisa, E.B. Ana, A.G. Ravelo, D.J. Yapu, A.G. Turba, Chem. Biodivers. 2, 264 (2005)

    Article  CAS  Google Scholar 

  11. P.G. Baraldi, S. Manfredini, D. Simoni, M.A. Tabrizi, J. Balzarini, E.D. Clercq, J. Med. Chem. 35, 1877 (1992)

    Article  CAS  Google Scholar 

  12. A. Kumar, R.A. Maurya, S.A. Sharma, P. Ahmad, A.B. Singh, G. Bhatia, A.K. Srivastava, Bioorg. Med. Chem. Lett. 19, 6447 (2009)

    Article  CAS  Google Scholar 

  13. W.O. Foye, Principi di Chemico Farmaceutica, vol. 416 (Piccin, Padora, 1991)

    Google Scholar 

  14. L.L. Andreani, E. Lapi, Bull. Chim. Farm. 99, 583 (1960)

    Google Scholar 

  15. Y.L. Zhang, B.Z. Chen, K.Q. Zheng, M.L. Xu, X.H. Lei, X.B. Yaoxue, Chem. Abstr. 96, 135383 (1982)

    Google Scholar 

  16. E.A.A. Hafez, M.H. Elnagdi, A.G.A. Elagamey, F.M.A.A. Eltaweel, Heterocycles 26, 903 (1987)

    Article  CAS  Google Scholar 

  17. A. Shaabani, R. Ghadari, A. Sarvary, A.H. Rezayan, J. Org. Chem. 74, 4372 (1982)

    Article  Google Scholar 

  18. M.N. Elinson, A.S. Dorofeev, F.M. Miloserdov, A.I. Ilovaisky, S.K. Feducovich, P.A. Belyakov, G.I. Nikishina, Adv. Synth. Catal. 350, 591 (2008)

    Article  CAS  Google Scholar 

  19. G.P. Ellis, in The Chemistry of Heterocyclic Compounds: Chromenes, Chromanes and Chromones, ed. by A. Weissberger, E.C. Taylor (Wiley, New York, 1977), p. 11

    Chapter  Google Scholar 

  20. S. Medda, S. Mukhopadhyay, M.K. Basu, J. Antimicrob. Chemother. 44, 791 (1999)

    Article  CAS  Google Scholar 

  21. M. Makino, Y. Fujimoto, Phytochemistry 50, 273 (1999)

    Article  CAS  Google Scholar 

  22. A.G.E. Amr, A.M. Mohamed, S.F. Mohamed, N.A. Abdel-Hafez, A.E.F.G. Hammam, Bioorg. Med. Chem. 14, 5481 (2006)

    Article  CAS  Google Scholar 

  23. S. Bhavanarushi, V. Kanakaiah, E. Yakaiah, V. Saddanapu, A. Addlagatta, V.J. Rani, Med. Chem. Res. 22, 2446 (2013)

    Article  CAS  Google Scholar 

  24. W. Kemnitzer, J. Drewe, S. Jiang, H. Zhang, C.C. Grundy, D. Labreque, M. Bubenick, G. Attardo, R. Denis, S. Lamothe, H. Gourdeau, B. Tseng, S. Kasibhatla, S.X. Cai, J. Med. Chem. 51, 417 (2008)

    Article  CAS  Google Scholar 

  25. M.N. Erichsen, T.H.V. Huynh, B. Abrahamsen, J.F. Bastlund, C. Bundgaard, O. Monrad, A.B. Jensen, C.W. Nielsen, K. Frydenvang, A.A. Jensen, L. Bunch, J. Med. Chem. 53, 7180 (2010)

    Article  CAS  Google Scholar 

  26. M. Mahmoodi, A. Aliabadi, S. Emami, M. Safavi, S. Rajabalian, A.M. Mohagheghi, A. Khoshzaban, A.S. Kermani, N. Lamei, A. Shafiee, A. Foroumadi, Arch. Pharm. Chem. Life Sci. 343, 411 (2010)

    Article  CAS  Google Scholar 

  27. C.W. Smith, J.M. Bailey, M.E.J. Billingham, S. Chandrasekhar, C.P. Dell, A.K. Harvey, C.A. Hicks, A.E. Kingston, G.N. Wishart, Bioorg. Med. Chem. 5, 2783 (1995)

    Article  CAS  Google Scholar 

  28. S.J. Tu, H. Jiang, Q.Y. Zhung, C.B. Miu, D.Q. Shi, X.S. Wang, Y. Gao, Chin. J. Org. Chem. 23, 488 (2003)

    CAS  Google Scholar 

  29. I. Devi, P.J. Bhuyan, Tetrahedron Lett. 45, 8625 (2004)

    Article  CAS  Google Scholar 

  30. J.M. Khurana, B. Nand, P. Saluja, Tetrahedron 66, 5637 (2010)

    Article  CAS  Google Scholar 

  31. M.M. Heravi, B.A. Jani, F. Derikvand, F.F. Bamoharram, H.A. Oskooie, Cat. Commun. 10, 272 (2008)

    Article  CAS  Google Scholar 

  32. S. Balalaie, M. Bararjanian, M. Sheikh-Ahmadi, S. Hekmat, P. Salehi, Synth. Commun. 37, 1097 (2007)

    Article  CAS  Google Scholar 

  33. A.T. Khan, M. Lal, S. Ali, M.M. Khan, Tetrahedron Lett. 52, 5327 (2011)

    Article  CAS  Google Scholar 

  34. J. Zheng, Li. Yiqun. Mendeleev Commun. 21, 280 (2011)

    Article  CAS  Google Scholar 

  35. S.S. Katkar, M.K. Lande, B.R. Arbad, S.T. Gaikwad, Chin. J. Chem. 29, 199 (2011)

    Article  CAS  Google Scholar 

  36. J.M. Khurana, S. Kumar, Tetrahedron Lett. 50, 4125 (2009)

    Article  CAS  Google Scholar 

  37. Y.M. Ren, C. Cai, Cat. Commun. 9, 1017 (2008)

    Article  Google Scholar 

  38. M. Seifi, H. Sheibani, Catal. Lett. 126, 275 (2008)

    Article  CAS  Google Scholar 

  39. S. Nemouchi, R. Boulcina, B. Carboni, A. Debache, C. R. Chim. 15, 394 (2012)

    Article  CAS  Google Scholar 

  40. I.A. Azath, P. Puthiaraj, K. Pitchumani, ACS Sustain. Chem. Eng. 1, 174 (2013)

    CAS  Google Scholar 

  41. A. Mobinikhaledi, N. Foroughifar, M.A. Bodaghi Fard, Syn. Res. Met-Org. Nano Met. Chem. 40, 179 (2010)

    CAS  Google Scholar 

  42. M.M. Heravi, A. Ghods, K. Bakhtiari, F. Derikvand, Synth. Commun. 1(40), 1927 (2010)

    Article  Google Scholar 

  43. M. Bihani, P.P. Bora, G. Bez, H. Askari, ACS Sustain. Chem. Eng. 1, 440 (2013)

    Article  CAS  Google Scholar 

  44. V.M. Joshi, L.M. Rupali, P.B. Throat, S.U. Tekale, B.R. Pati, M.P. Kale, R.P. Pawar, Chin. Chem. Lett. 25, 455 (2014)

    Article  CAS  Google Scholar 

  45. M. Khoobi, L. Mamani, F. Rezazadeh, Z. Zareie, A. Foroumadi, A. Ramazani, A. Shafiee, J. Mol. Catal. A Chem. 359, 74 (2012)

    Article  CAS  Google Scholar 

  46. S. Balalaielalaie, M. Bararjanian, A.M. Amani, B. Movassagh, Synlett 2, 0263 (2006)

    Article  Google Scholar 

  47. M.M. Khodaei, K. Bahrami, A. Farrokhi, Synth. Commun. 40, 1492 (2010)

    Article  CAS  Google Scholar 

  48. G. Brahmachari, B. Banerjee, ACS Sustain. Chem. Eng. 2, 411 (2014)

    Article  CAS  Google Scholar 

  49. A.L. Lehninger, D.L. Nelson, M.M. Cox, Principles of Biochemistry, 3rd edn. (Worth Publishers, New York, 2000), p. 1255

    Google Scholar 

  50. E. Topo, A. Soricelli, A.D. Aniello, S. Ronsini, G.D. Aniello, Reprod. Biol. Endocrinol. 7, 1 (2009)

    Article  Google Scholar 

  51. S. Budava, The Merck Index: An Encyclopedia of Chemicals, Drugs, and Biological, 11th edn. (Merck, Rahway, 1989)

  52. Nomenclature and symbolism for amino acids and petides, Pure Appl. Chem. 56, 595–624 (1983)

    Google Scholar 

  53. A. Ahad, M. Farooqui, Chem. Biol. Interface 5, 301 (2015)

    CAS  Google Scholar 

  54. A. Ahad, M. Farooqui, Chem. Sci. Trans. 5, 202 (2016)

    CAS  Google Scholar 

  55. A. Ahad, M. Farooqui, Iran J. Org. 8, 1685 (2016)

    Google Scholar 

  56. A. Ahad, M. Farooqui, Org. Prep. Proc. Int. 48, 371 (2016)

    Article  CAS  Google Scholar 

  57. R. Ramtekkar, K. Kumarvel, G. Vasuki, K. Sekar, R. Krishna, Lett. Drug Des. Discov. 6, 579 (2009)

    Article  CAS  Google Scholar 

  58. N. Foloppe, L.M. Fisher, R. Howes, A. Potter, A.G.S. Robertson, A.E. Surgenor, Bioorg. Med. Chem. 14, 4792 (2006)

    Article  CAS  Google Scholar 

  59. B. Datta, M.A. Pasha, Ultrason. Sonochem. 19, 725 (2012)

    Article  CAS  Google Scholar 

Download references

Acknowledgments

Laboratory facilities and financial assistance from the Postgraduate and Research Centre, Dr. Rafiq Zakaria Campus, Maulana Azad College is gratefully acknowledged. We are also grateful to SAIF Punjab University and YB Chavhan College of Pharmacy, Aurangabad, for providing analytical facilities.

Author information

Authors and Affiliations

  1. Post Graduate and Research Center, Dr. Rafiq Zakaria Campus, Maulana Azad College, Rouza Baugh, Aurangabad, M.S, India

    Abdul Ahad & Maqdoom Farooqui

Authors
  1. Abdul Ahad
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Maqdoom Farooqui
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to Maqdoom Farooqui.

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Ahad, A., Farooqui, M. Organocatalyzed domino reactions: diversity oriented synthesis of pyran-annulated scaffolds using in situ-developed benzylidenemalononitriles. Res Chem Intermed 43, 2445–2455 (2017). https://doi.org/10.1007/s11164-016-2772-8

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s11164-016-2772-8

Keywords

Search

Navigation