A green, efficient, and rapid procedure for the synthesis of 2-amino-3-cyano-1,4,5,6-tetrahydropyrano[3,2-c]quinolin-5-one derivatives catalyzed by ammonium acetate

Tetrahedron Letters

Volumn 52, Issue 20, 2011, Pages 2597-2600

  Lei, Min ^a   Ma, Lei ^b   Hu, Lihong ^a  

^a SHANGHAI INSTITUTE OF MATERIA MEDICA   (China)

^b EAST CHINA UNIVERSITY OF SCIENCE AND TECHNOLOGY   (China)

Author keywords

4 Hydroxyquinolin 2(1H) one; Aldehyde; Green chemistry; Malononitrile; Multi component reaction

Indexed keywords

2 AMINO 3 CYANO 1,4,5,6 TETRAHYDROPYRANO[3,2 C]QUINOLIN 5 ONE DERIVATIVE; 4 HYDROXYQUINOLIN 2(1H) ONE; AMMONIUM ACETATE; BENZALDEHYDE; MALONONITRILE; QUINOLINE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CATALYSIS; CYCLIZATION; DRUG STRUCTURE; DRUG SYNTHESIS; ISOMERIZATION; KNOEVENAGEL CONDENSATION; MICHAEL ADDITION; ONE POT SYNTHESIS;

EID: 79955065509     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2011.03.061     Document Type: Article

References (35)

1. A. Strecker Liebigs Ann. Chem. 75 1850 27 45
2. M. Lei, L. Ma, and L. Hu Monatsh. Chem. 141 2010 1005 1008
3. V. Nair, P.B. Beneesh, V. Sreekumar, S. Bindu, R.S. Menon, and A. Deepthi Tetrahedron Lett. 46 2005 201 203
4. J.-N. Tan, M. Lia, and Y. Gu Green Chem. 12 2010 908 914
5. S.K. De, and R.A. Gibbs Synthesis 2005 1748 1750
6. C.-M. Yang, M. Jeganmohan, K. Parthasarathy, and C.-H. Cheng Org. Lett. 12 2010 3610 3613
7. C. Yu, M. Lei, W. Su, and Y. Xie Synth. Commun. 37 2007 3301 3309
8. M. Lei, L. Ma, and L. Hu Tetrahedron Lett. 50 2009 6393 6397
9. M. Lei, L. Ma, and L. Hu Tetrahedron Lett. 51 2010 4746 4749
10. Y. Tang, J. Oppenheimer, Z. Song, L. You, X. Zhang, and R.P. Hsung Tetrahedron 62 2006 10785 10813
11. T.C. McKee, R.W. Fuller, C.D. Covington, J.H. Cardellina II, R.J. Gulakowski, B.L. Krepps, J.B. McMahon, and M.R. Boyd J. Nat. Prod. 59 1996 754 758;
12. T.C. McKee, C.D. Covington, R.W. Fuller, H.R. Bokesch, S. Young, J.H. Cardellina II, M.R. Kadushin, D.D. Soejarto, P.F. Stevens, G.M. Cragg, and M.R. Boyd J. Nat. Prod. 61 1998 1252 1256
13. S.-J. Wu, and I.-S. Chen Phytochemistry 34 1993 1659 1661
14. E.J. Jung, B.H. Park, and Y.R. Lee Green Chem. 12 2010 2003 2011
15. S. Kumar, D. Hernandez, B. Hoa, Y. Lee, J.S. Yang, and A. McCurdy Org. Lett. 10 2008 3761 3764
16. M. Rawat, V. Prutyanov, and W.D. Wulff J. Am. Chem. Soc. 128 2006 11044 11053
17. O.A. Fedorova, F. Maure, A.V. Chebunkova, Y.P. Strokach, T.M. Valova, L.G. Kuzmina, J.A.K. Howard, M. Wenzel, K. Gloe, V. Lokshin, and A. Samat J. Phys. Org. Chem. 20 2007 469 483
18. J.D. Hepworth, and B.M. Heron Prog. Heterocycl. Chem. 17 2005 33 62
19. S. Delbaer, J.-C. Micheau, and G. Vermeersch J. Org. Chem. 68 2003 8968 8973
20. C.N. O'Callaghan, and T.B.H. McMurry J. Chem. Res., Synop. 1995 214 and J. Chem. Res. (M), 1995, 1448 and references cited therein
21. A.H. Adbel-Fattah, A.M. Hesien, S.A. Metwally, and M.H. Elnagdi Liebigs Ann. Chem. 1989 585 588
22. J.M. Quintela, C. Peinador, and M.J. Moreira Tetrahedron 51 1995 5901 5912
23. S. Srivastava, S. Batra, and A.P. Bhaduri Indian J. Chem., Sect. B 35B 1996 602 604
24. Y. Peng, and G. Song Catal. Commum. 8 2007 111 114
25. X.-S. Wang, Z.-S. Zeng, M.-M. Zhang, Y.-L. Li, D.-Q. Shi, S.-J. Tu, X.-Y. Wei, and Z.-M. Zong J. Chem. Res. 2006 228 230
26. N.S. Ibrahim Heterocycles 24 1986 935 938
27. N.S. Babu, N. Pasha, K.T.V. Rao, P.S.S. Prasad, and N. Lingaiah Tetrahedron Lett. 49 2008 2730 2733
28. X. Wang, Z. Zeng, D. Shi, X. Wei, and Z. Zong Synth. Commun. 34 2004 3021 3027
29. W. Su, J. Li, Z. Zheng, and Y. Shen Tetrahedron Lett. 46 2005 6037 6040
30. J. Peng, and Y. Deng Tetrahedron Lett. 42 2001 5917 5919
31. R. Zheng, X. Wang, H. Xu, and J. Du Synth. Commun. 36 2006 1503 1513
32. Y. Peng, G. Song, and F. Huang Monatsh. Chem. 136 2005 727 731
33. M.M. Heravi, M.H. Tehrani, K. Bakhtiari, and H.A. Oskooie J. Chem. Res. 2006 561 562
34. D. Kumar, V.B. Reddy, S. Sharad, U. Dube, and S. Kapur Eur. J. Med. Chem. 44 2009 3805 3809
35. +.