A facile transformation of 2-aminochromone to 4-chlorocoumarin and its reaction with ethylenediamine

Journal of Chemical Research

Volumn , Issue 10, 2006, Pages 651-654

  Ghosh, Tarun ^a   Sur, Kumar Ranabir ^a   Bandyopadhyay, Chandrakanta ^a  

^a RAMAKRISHNA MISSION VIVEKANANDA CENTENARY COLLEGE   (India)

Author keywords

1,4 diazepines; 2 aminochromones; Biscoumarins; Coumarins

Indexed keywords

EID: 33750944712     PISSN: 03082342     EISSN: None     Source Type: Journal    
DOI: 10.3184/030823406779173505     Document Type: Article

References (29)

1. (a) R.K. Smalley, Comprehensive Organic Chemistry, eds D. Barton and W.D. Ollis, Pergamon, 1979, vol. 4, 600;
2. (b) H. Schultz, Benzodiazepines: Springer, 1982, vol. 2, 240;
3. (c) J.K. Landquist, Comprehensive Heterocyclic Chemistry, ed. A.R. Katritzky and C.W. Rees, Pergamon, 1984, vol. 1, 166;
4. (d) D. Lloyd and H. McNab, Adv. Heterocyclic Chem., 1998, 71, 1.
5. J.R. De Baun, F.M. Pallos and D.R. Baker, U S Patent, 1976, 3,978,227; Chem. Abstr., 1977, 86, 5498d.
6. (a) L.H. Sternbach, Drug Res., 1978, 22, 229;
7. (b) L.H. Sternbach, J. Med. Chem., 1979, 22, 1.
8. M. Hamdi, O. Grech, R. Sakellariou and V. Speziale, J. Heterocycl. Chem., 1994, 31, 509.
9. M. Hamdi, S. Cottet, C. Tedeschi and V. Speziale, J. Heterocycl. Chem., 1997, 34, 1821.
10. (a) S.K. Gorozhankin, M.A. Kirpichenok and I.I. Grandberg, Khim. Geterosikl. Soedin, 1990, 1326;
11. (b) A. Alberola, B. Calvo, A. Gonzalez-Ortega and R. Pedrosa, J. Chem. Soc. Perkin Trans. 1, 1992, 3075.
12. G.M. Vishnyakova and L.A. Tarakanova, Zh. Obshch. Khim., 1991, 61, 2123.
13. V.V. Mulwad and B.S. Mahaddalkar, Indian J. Chem., 1999, 38B, 29.
14. T.Y. Mozhaeva, N.L. Nam, V.P. Lezina, V.L. Savel'ev, V.N. Knyazev and V.N. Drozd, Zh. Org. Khim., 1992, 28, 2127.
15. V.N. Drozd, N.L. Nam, V.N. Knyazev, D.S. Yufit, Y.T. Struchkov, T.Y. Mozhaeva, V.P. Lezina and V.L. Savel'ev, Zh. Org. Khim., 1992, 28, 1496.
16. T.Y. Mozhaeva, V.P. Lezina, V.L. Savel'ev, N.L. Nam, V.N. Knyazev and V.N. Drozd, Zh. Org. Khim., 1992, 28, 1489.
17. T. Ghosh, S. Saha and C. Bandyopadhyay, Synthesis, 2005, 1845.
18. (a) V.A. Zagorevskii and D.A. Zykov, Zhur. Obshch. Khim., 1960, 30, 3100;
19. (b) V.A. Zagorevskii, D.A. Zykov and E.K. Orlova, Zhur. Obshch. Khim., 1961, 31, 568;
20. (c) V.A. Zagorevskii and E.K. Orlova, Zhur. Obshch. Khim., 1963, 33, 1857.
21. S.M. Golzman, L.A. Zhmurenko and V.A. Zagorevskii, Russ. Chem. Pharm. J., 1971, 5, 264.
22. (a) W. Stadlbauer, Monatsh Chem., 1986, 117, 1305;
23. (b) K.N. Trivedi, S.S. Madhava Rao, S.V. Mistry and S.M. Desai, J. Ind. Chem. Soc., 2001, 78, 579 and references therein;
24. (c) K.C. Majumdar and T. Bhattacharyya, Tetrahedron Lett., 2001, 42, 4231.
25. L. Gruber, I. Tomoskozi and L. Redics, Synthesis, 1975, 708.
26. T. Ghosh and C. Bandyopadhyay, J. Heterocycl. Chem., 2006, 43, in press.
27. (a) M.A. Kirpichenok, S.K. Gorozhamkin and I.I. Grandberg, Khim. Geterosikl. Soedin, 1990, 836;
28. (b) H. Hishmat, A.M. Gohar, M.E. Wassef, N.M.A. El-El-rashi and A.A. Nawar, Justus Liebigs Ann. Chem., 1966, 692, 166.
29. D.T. Connor, P.A. Young and M. von Strandtman, Synthesis, 1978, 208.