Molecular Diversity

, Volume 18, Issue 1, pp 111–117 | Cite as

Synthesis of new 1,5-diaryl-3-(arylamino)-1H-pyrrol-2(5H)-ones under catalyst-free and solvent-free conditions

Full-Length Paper
First Online:
Received:
Accepted:

Abstract

Several new 1,5-diaryl-3-(arylamino)-1H-pyrrol-2(5H)-ones were synthesized via the three-component condensation reaction of aldehydes, aromatic amines, and ethyl pyruvate under catalyst-free and solvent-free conditions. Also, 5-(4-hydroxyl-3-nitrophenyl)-1-(4-methoxy-phenyl)-3-(4-methoxyphenylamino)-1,5-dihydro-pyrrol-2-one was synthesized using oxime instead of aldehyde. The eco-friendly, simple procedure, green procedure, catalyst-free and solvent-free conditions, short reaction times, and high yields of the products are the advantages of this method.

Keywords

1H-Pyrrol-2(5H)-ones Catalyst-free Lactams Solvent-free MCRs MCC 4MCR 
This is a preview of subscription content, log in to check access.

Notes

Acknowledgments

The authors are thankful to the Persian Gulf University Research Council for partial support of this study.

Supplementary material

11030_2013_9496_MOESM1_ESM.doc (6.3 mb)
Supplementary material 1 (doc 6431 KB)

References

  1. 1.
    Morin RB, Gorman M (1982) Chemistry and biology of \(\beta \)-lactam antibiotics. Academic Press, New YorkGoogle Scholar
  2. 2.
    Trofimov BA, Sobenina LN, Demenev AP, Mikhaleva AI (2004) C-vinylpyrroles as pyrrole building blocks. Chem Rev 104:2481–2506. doi: 10.1021/cr020100i PubMedCrossRefGoogle Scholar
  3. 3.
    Gein VL, Popov AV, Kolla VE, Popova NA, Potemkin KD (1993) Synthesis and biological activity of 1,5-diaryl-3-arylamino-4-carboxymethyl-2,5-dihydro-2-pyrrolones and 1,5-diaryl-4-carboxymethyltetrahydropyrrole-2,3-diones. Pharm Chem J 27:343–346CrossRefGoogle Scholar
  4. 4.
    Gein VL, Popov AV, Kolla VE, Popova NA (1993) Synthesis and biological activity of 1,5-diaryl-3-alkylamino-4-carboxymethyl-2,5-dihydropyrrol-2-ones and 1,5-diaryl-4-carboxymethyltetrahydro-pyrrol-2,3-diones. Pharmazie 48:107–109Google Scholar
  5. 5.
    Becker I (2004) Preparation of pyrrole and pyrrolidine derivatives of pyrimidine. 1-(2- pyrimidinyl)pyrrole-an inhibitor of X. Phaseoli and X. Malvacearum. J Heterocyclic Chem 41:343–348. doi: 10.1002/jhet.5570410306
  6. 6.
    Khalaf AI, Waigh RD, Drummond AJ, Pringle B, McGroarty I, Skellern GG, Suckling CJ (2004) Distamycin analogues with enhanced lipophilicity: synthesis and antimicrobial activity. J Med Chem 47:2133–2156. doi: 10.1021/jm031089x PubMedCrossRefGoogle Scholar
  7. 7.
    Toja E, Gorini C, Zirotti C, Barzaghi F, Galliani G (1991) Amnesia-reversal activity of a seris of 5-alkoxy-1-arylcarbonyl-2-pyrrolidinones and 5-alkoxy-1-arylmethyl-2-pyrrolidinones. Eur J Med Chem 26:415–422. doi: 10.1016/0223-5234(91)90102-S CrossRefGoogle Scholar
  8. 8.
    Kocharyan, S.T.; Churkina, N. P.; Razina, T. L.; Karapetyan, V. E.; Ogandzhanyan, S. M.; Voskanyan, V. S.; Babayan, A. T. Khim Geterotsikl (1994) Soedin 1345. doi: 10.1007/s11164-012-0749-9
  9. 9.
    Vaughan WR, Tripp RC (1960) 1,5-Diary1-2,3-pyrrolidinediones. XII. Enamines and the pseudo-pyrrolidinediones. J Am Chem Soc 82:4370–4376. doi: 10.1021/ja01501a064 CrossRefGoogle Scholar
  10. 10.
    Wu YC, Liu L, Wang D, Chen YJ (2006) Efficient synthesis of 3-arylaminopyrroline-2-ones by the tandem reaction of anilines and \(\beta , \gamma \)-unsaturated \(\alpha \)-ketoesters. J Heterocycl Chem 34:949–955. doi: 10.1002/jhet.5570430421
  11. 11.
    Palacios F, Vicario J, Aparicio D (2006) An efficient synthesis of achiral and chiral cyclic dehydro-\(\alpha \)-amino acid derivatives through nucleophilic addition of amines to \(\beta ,\,\gamma \)-unsaturated\(\alpha \)-keto esters. Eur J Org Chem 2843–2850: doi: 10.1002/ejoc.200600092
  12. 12.
    Li X, Deng H, Luo S, Cheng JP (2008) NAP ether mediated intramolecular aglycon delivery: a unified strategy for 1,2-cis-glycosylation. Eur J Org Chem 4350–4356. doi: 10.1002/ejoc.200800249
  13. 13.
    Ghashang M, Shaterian HR (2011) A convenient method for the preparation of 1,5-diaryl-3-(arylamino)-1H-pyrrol-2(5H)-ones. Chin J Chem 29:1851–1855. doi: 10.1002/cjoc.201180323 CrossRefGoogle Scholar
  14. 14.
    Niknam K, Jamali A (2012) Silica-bonded \(N\)-propylpiperazine sodium \(n\)-propionate as recyclable basic catalyst for synthesis of 3,4-dihydropyrano[\(c\)]chromene derivatives and biscoumarins. Chin J Catal 33:1840–1849. doi:  10.1016/S1872-2067(11)60457-9 CrossRefGoogle Scholar
  15. 15.
    Niknam K, Deris A, Panahi F (2013) Silica-functionalized N-propylpiperazine for immobilization of palladium nanoparticles as efficient heterogeneous catalyst for cyanation reactions. Chin J Catal 34:718–722. doi: 10.1016/S1872-2067(12)60532-4 Google Scholar
  16. 16.
    Niknam K, Deris A, Naeimi F, Majleci F (2011) Synthesis of 1,2,4,5-tetrasubstituted imidazoles using silica-bonded propylpiperazine N-sulfamic acid as a recyclable solid acid catalyst. Tetrahedron Lett 52:4642–4645. doi: 10.1016/j.tetlet.2011.06.105 Google Scholar
  17. 17.
    Niknam K, Gharavi A, Hormozi-Nezhad MR, Panahi F, Sharbati MT (2011) Synthesis of 1,2,4,5-tetrasubstituted imidazoles using silica-bonded propylpiperazine N-sulfamic acid as a recyclable solid acid catalyst. Synthesis 1609–1615. doi: 10.1055/s0030-1259996
  18. 18.
    Niknam K, Sadeghi Habibabad M, Deris A, Aeinjamshid N (2013) Preparation of silica-bonded N- propyltriethylenetetramine as a recyclable solid base catalyst for the synthesis of 4,4\(^{^{\prime }}\)-(arylmethylene)bis(1H-pyrazol-5-ols). Monatsh Chem 144:987–992. doi: 10.1007/s00706-012-0910-6 Google Scholar
  19. 19.
    Niknam K, Jamali A, Tajaddod M, Deris A (2012) Synthesis of 2-amino-4,6-diarylnicotinonitriles using silica-bound N-propyl triethylenetetramine sulfamic acid as a recyclable solid acid catalyst. Chin J Catal 33:1312–1317. doi: 10.1016/S1872-2067(11)60421-X Google Scholar
  20. 20.
    Niknam K, Saberi D, Nouri Sefat M (2009) Silica-bonded S-sulfonic acid as a recyclable catalyst for chemoselective synthesis of 1,1-diacetates. Tetrahedron Lett 50:4058–4062. doi: 10.1016/j.tetlet.2009.04.096 Google Scholar
  21. 21.
    Niknam K, Saberi D (2009) Silica-bonded N-propyl sulfamic acid as an efficient catalyst for the formylation and acetylation of alcohols and amines under heterogeneous conditions. Tetrahedron Lett 50:5210–5214. doi: 10.1016/j.tetlet.2009.06.140 CrossRefGoogle Scholar

Copyright information

© Springer Science+Business Media Dordrecht 2013

Authors and Affiliations

  1. 1.Department of Chemistry, Faculty of SciencesPersian Gulf UniversityBushehrIran

Personalised recommendations