Efficient one-pot synthesis of 4-aryl-3-cyano-2,5-dihydro-1H-indeno[1,2-b] pyridin-2-one and 4-aryl-3-cyano-1,2,5,6-tetrahydrobenzo[h]quinolin-2-one derivatives under solvent-free conditions

Synthetic Communications

Volumn 39, Issue 6, 2009, Pages 1027-1034

  Rong, Liangce ^a,b   Han, Hongxia ^a   Jiang, Hong ^b   Zhang, Qiya ^a   Tu, Shuajiang ^a,b  

^a JIANGSU NORMAL UNIVERSITY   (China)

^b JIANGSU NORMAL UNIVERSITY   (China)

Author keywords

2 Cyanoacetamide; 3 cyano 2 pyridones; One pot reactions; Solvent free; Synthesis

Indexed keywords

3 CYANO 1,2,5,6 TETRAHYDROBENZO[H]QUINOLIN 2 ONE DERIVATIVE; 3 CYANO 2,5 DIHYDRO 1H INDENO[1,2 B]PYRIDIN 2 ONE; 3,4 DIHYDRONAPHTHALEN 1(2H) ONE; ACETAMIDE DERIVATIVE; ALDEHYDE; CYANOACETAMIDE; INDAN DERIVATIVE; NAPHTHALENE DERIVATIVE; PYRIDINE DERIVATIVE; QUINOLINE DERIVATIVE; SODIUM HYDROXIDE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL STRUCTURE; ONE POT SYNTHESIS;

EID: 60849087358     PISSN: 00397911     EISSN: 15322432     Source Type: Journal    
DOI: 10.1080/00397910802463878     Document Type: Article

References (13)

1. (a) Varma, R. S. Clay and clay-supported reagents in organic synthesis. Tetrahedron 2002, 58, 1235-1255;
2. (b) Tanaka, K. Solvent-Free Organic Synthesis; Wiley-VCH: Weinheim, Germany, 2003.
3. Tanaka, K.; Toda, F. Solvent-free organic synthesis. Chem. Rev. 2000, 100, 1025-1074.
4. (a) Weber, L.; Illegen, K.; Almstetter, M. Discovery of new multi component reactions with combinatorial methods. Synlett 1999, 366-374;
5. (b) Armstrong, R. W.; Combs, A. P.; Tempest, P. A.; Brown, S. D.; Keating, T. A. Multiple-component condensation strategies for combinatorial library synthesis. Acc. Chem. Rev. 1996, 29, 123-131.
6. (a) Rong, L. C.; Li, X. Y.; Wang, H. Y.; Shi, D. Q.; Tu, S. J. An efficient and facile synthesis of 2-amino-4,6-diarylbenzene-1,3-dicarbonitrile and 1,2-dihydro-2-oxo-4,6-diarylpyridine-3-carbonitrile under solvent-free conditions. Chem. Lett. 2006, 35, 1314-1315;
7. (b) Rong, L. C.; Wang, H. Y.; Shi, J. W.; Yang, F.; Yao, H.; Tu, S. J.; Shi, D. Q. An efficient and facile procedure for the synthesis of 4,6-Diaryl-2(1H)-pyridones under solvent-free conditions. J. Heterocycl. Chem. 2007, 44(10), 1505-1508;
8. (c) Rong, L. C.; Han, H. X.; Yang, F.; Yao, H.; Jiang, H.; Tu, S. J. An efficient one-pot synthesis of 2-amino-4,6-diarylbenzene-1,3-dicarbonitrile under solvent-free conditions. Synth. Commun. 2007, 37(21), 3767-3772.
9. Siedel, M. C.; Viste, K. L.; Yih, R. Y. Plant growth inhibition with N-aryl-pyrid-2-ones. U. S. Patent 3,761,240, September 25, 1973. 6. Misic-Vukovic, M.; Mijin, D.; Radojkovic-Velickovic, M.; Valentic, N.; Krstic, V. Condensation of 1,3-diketones with cyanoacetamide: 4,6-Disubstituted-3-cyano- 2-pyridones. J. Serb. Chem. Soc. 1998, 63(8), 585-599.
10. Paulvannan, K.; Chen, T. Solid-phase synthesis of 1,2,3,4-tetrahydro-2- pyridones via aza-annulation of enamines. J. Org. Chem. 2000, 65, 6160-6166;
11. (b) Dave, C. G.; Shah, D. A.; Agrawal, Y. K. A simple and convenient synthesis of 4,6-disubstituted 3-cyanopyridin-2(1H)-ones under solvent-free microwave conditions. Ind. J. Chem. 2004, 43B(4), 885-887;
12. (c) Alberola, A.; Calvo, L. A.; Ortega, A. G.; Ruiz, M. C. S.; Yustos, P. Regioselective synthesis of 2(1H)-pyridinones from â-aminoenones and malononitrile: Reaction mechanism. J. Org. Chem. 1999, 64, 9493-9498.
13. -3.