Highly efficient conversion of fused 2-amino-4-aryl-4H-chromene-3- carbonitriles into fused 2-oxo-4-aryl-2H-chromene-3-carbonitriles using Vilsmeier conditions

Tetrahedron Letters

Volumn 54, Issue 29, 2013, Pages 3862-3864

  Banothu, Janardhan ^a   Velpula, Ravibabu ^a   Gali, Rajitha ^a   Bavantula, Rajitha ^a   Crooks, Peter A ^b  

^a NATIONAL INSTITUTE OF TECHNOLOGY   (India)

^b UNIVERSITY OF ARKANSAS FOR MEDICAL SCIENCES   (United States)

Author keywords

Fused 2 amino 4 aryl 4H chromene 3 carbonitrile; Fused 2 oxo 4 aryl 2H chromene 3 carbonitriles; Vilsmeier conditions

Indexed keywords

2 OXO 4 ARYL 2H CHROMENE 3 CARBONITRILE DERIVATIVE; COUMARIN DERIVATIVE; CYANIDE; GEIPARVARIN; NOVOBIOCIN; UNCLASSIFIED DRUG; WARFARIN;

ARTICLE; BIOTRANSFORMATION; DRUG SYNTHESIS; REACTION TIME; STRUCTURE ANALYSIS; VILSMEIER HAACK REACTION;

EID: 84879030331     PISSN: 00404039     EISSN: 18733581     Source Type: Journal    
DOI: 10.1016/j.tetlet.2013.05.030     Document Type: Article

References (44)

1. P. Laurin, D. Ferroud, M. Klich, C. Dupuis-Haelin, P. Mauvais, P. Lassaigne, A. Bonnefoy, and B. Musicki Bioorg. Med. Chem. Lett. 9 1999 2079 2084
2. J.R.S. Hoult, and M. Paya Gen. Pharmacol. 27 1996 713 722
3. A.A. Emmanuel-Giota, K.C. Fylaktakidou, D.J. Hadjipavlou-Litina, K.E. Litinas, and D.N. Nicolaides J. Heterocycl. Chem. 38 2001 717 722
4. C.J. Wang, Y.J. Hsieh, C.Y. Chu, Y.L. Lin, and T.H. Tseng Cancer Lett. 183 2002 163 168
5. Z.M. Nofal, M.I. El-Zahar, and S.S. Abd El-Karim Molecules 5 2000 99 113
6. H. Hoeksema, J.L. Johnson, and J.W. Hinman J. Am. Chem. Soc. 77 1955 6710 6711
7. C.G. Smith, A. Dietz, W.T. Sokolski, and G.M. Savage Antibiot. Chemother. 6 1956 135 142
8. A. Carotti, A. Carrieri, S. Chimichi, M. Boccalini, B. Cosimelli, C. Gnerre, A. Carotti, P.A. Carrupt, and B. Testa Bioorg. Med. Chem. Lett. 12 2002 3551 3555
9. K.V. Sashidhara, K. Abdhesh, K. Manoj, S. Ravi, B. Gitika, and A.K. Khanna Bioorg. Med. Chem. Lett. 20 2010 4248 4251
10. K.V. Sashidhara, K. Abdhesh, K. Manoj, A. Srivastava, and A. Puri Bioorg. Med. Chem. Lett. 20 2010 6504 6507
11. I. Manolov, and N.D. Danchev Eur. J. Med. Chem. Chim. Ther. 30 1995 531 536
12. Y. Kashman, K.R. Gustafson, R.W. Fuller, J.H. Cardellina, J.B. McMahon, M.J. Currens, R.W. Buckheit Jr., S.H. Hughes, G.M. Cragg, and M.R. Boyd J. Med. Chem. 35 1992 2735 2743
13. S. Kirkiacharian, D.T. Thuy, S. Sicsic, R. Bakhchinian, R. Kurkjian, and T. Tonnaire Il Farmaco 57 2002 703 708
14. M.J. Currens, J.M. Mariner, J.B. McMahon, and M.R. Boyd J. Pharmacol. Exp. Ther. 279 1996 652 661
15. R.O. Kennedy, and R.D. Thornes Coumarins: Biology, Applications and Mode of Action 1997 Wiley & Sons Chichester, UK
16. M. Zahradnik The Production and Applications of Fluorescent Brightening Agent 1992 Wiley & Sons Chichester, UK
17. H. Von Pechmann, and C. Duisberg Chem. Ber. 16 1883 2119 2128
18. H. Von Pechmann Chem. Ber. 17 1884 929 979
19. E.V.O. John, and S.S. Israelstam J. Org. Chem. 26 1961 240 242
20. P.R. Singh, D.U. Singh, and S.D. Samant Synlett 2004 1909 1912
21. E. Knoevenagel Chem. Ber. 29 1896 172 174
22. A. Shockravi, H. Shargi, H. Valizadeh, and M.M. Heravi Phosphorus, Sulfur Silicon Relat. Elem. 177 2002 2555 2559
23. A. Song, X. Wang, and K.S. Lam Tetrahedron Lett. 44 2003 1755 1758
24. N. Cairns, L.M. Harwood, and D.P. Astles J. Chem. Soc., Perkin Trans. 1 1994 3101 3107
25. W.H. Perkin, and W. Henry Sr. J. Chem. Soc. 28 1875 10 11
26. J.R. Johnson Org. React. 1 1942 210 265
27. A. Maercker Org. Synth. 14 1934 270 291
28. G. Wittig, and W. Haag Chem. Ber. 88 1955 1654 1666
29. I. Yavari, R. Hekmat-shoar, and A. Zonouzi Tetrahedron Lett. 39 1998 2391 2392
30. R.L. Shriner Org. React. 1 1942 15 46
31. M.R. Saidi, and K. Bigdeli J. Chem. Res. (S) 1998 800 801
32. K. Philip, F. Xiangshu, and V. John Synth. Commun. 32 2002 1135 1144
33. H. Valizadeh, A. Shockravi, and H. Gholipur J. Heterocycl. Chem. 44 2007 867 870
34. B.V. Kumar, H.S.B. Naik, D. Girija, and B.V. Kumar J. Chem. Sci. 123 2011 615 621
35. A.A. Fadda, M.T. Zeimaty, M.M. Gerges, H.M. Refat, and E.R. Biehl Heterocycles 43 1996 23 32
36. R.M. Santhosh, A. Manjula, R.B. Vittal, B.N. Jagadeesh, K.L. Santosh, and Y. Soujanya J. Org. Chem. 77 2012 10648 10654
37. K. William, J. Songchun, Z. Hong, K. Shailaja, C.-G. Candace, B. Charles, A. Giorgio, D. Real, L. Serge, G. Henriette, T. Ben, D. John, and X.C. Sui Bioorg. Med. Chem. Lett. 18 2008 5571 5575
38. M.S. Nermien, M.M. Hany, S.A.E.H.K. Essam, S.M. Shymaa, and M. E.-A. Ahmed Eur. J. Med. Chem. 46 2011 765 772
39. B.S. Kuarm, Y.T. Reddy, J.V. Madhav, P.A. Crooks, and B. Rajitha Bioorg. Med. Chem. Lett. 21 2011 524 527
40. S.V. Laxmi, Y.T. Reddy, B.S. Kuarm, P.N. Reddy, P.A. Crooks, and B. Rajitha Bioorg. Med. Chem. Lett. 21 2011 4329 4331
41. B. Janardhan, and B. Rajitha Chin. Chem. Lett. 23 2012 1015 1018
42. A.M. Ramadan, and U.S. Kamal J. Heterocycl. Chem. 46 2009 149 151
43. J.T. Nilesh, and P.P. Manish ARKIVOC xiii 2009 363 380
44. M.M. Ghorab, S.M. Abdel-Gawad, and M.S.A. El-Gaby Il Farmaco 55 2000 249 255