A reinvestigation of the reactions of 3-substituted chromones with hydroxylamine. Unexpected synthesis of 3-amino-4H-chromeno[3,4-d]isoxazol-4-one and 3-(diaminomethylene)chroman-2,4-dione

Tetrahedron Letters

Volumn 49, Issue 48, 2008, Pages 6856-6859

  Sosnovskikh, Vyacheslav Ya ^a   Moshkin, Vladimir S ^a   Kodess, Mikhail I ^b  

^a URAL FEDERAL UNIVERSITY   (Russian Federation)

^b INSTITUTE OF ORGANIC SYNTHESIS   (Russian Federation)

Author keywords

2 Aminochromone 3 carboxamide; 3 (Diaminomethylene)chroman 2,4 dione; 3 Amino 4H chromeno 3,4 d isoxazol 4 one; 3 Substituted chromones; Hydroxylamine

Indexed keywords

2 AMINOCHROMONE 3 CARBOXAMIDE; 3 (DIAMINOMETHYLENE)CHROMAN 2,4 DIONE; 3 AMINO 4H CHROMENO[3,4 D]ISOXAZOL 4 ONE; 3 CYANOCHROMONE; 3 FORMYLCHROMONE; 3 FORMYLCHROMONE 3 OXIME; CHROMONE DERIVATIVE; HYDROXYLAMINE; UNCLASSIFIED DRUG;

ARTICLE; SYNTHESIS;

EID: 53549111605     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2008.09.091     Document Type: Article

References (38)

1. Horton D.A., Bourne G.T., and Smythe M.L. Chem. Rev. 103 (2003) 893-930
2. Nohara A., Kuriki H., Saijo T., Sugihara H., Kanno M., and Sanno Y. J. Med. Chem. 20 (1977) 141-145
3. Nohara A., Umetani T., Ukawa K., and Sanno Y. Chem. Pharm. Bull. 22 (1974) 2959-2965
4. Ukawa K., Ishiguro T., Wada Y., and Nohara A. Heterocycles 24 (1986) 1931-1941
5. Hsung R.P. J. Org. Chem. 62 (1997) 7904-7905
6. Hsung R.P., Zificsak C.A., Wei L.-L., Zehnder L.R., Park F., Kim M., and Tran T.-T.T. J. Org. Chem. 64 (1999) 8736-8740
7. Sosnovskikh V.Ya., Irgashev R.A., and Levchenko A.A. Tetrahedron 64 (2008) 6607-6614
8. Ghosh C.K. J. Heterocycl. Chem. 20 (1983) 1437-1445
9. Sabitha G. Aldrichim. Acta 29 (1996) 15-25
10. Ghosh C.K. Heterocycles 63 (2004) 2875-2898
11. Gašparová R., and Lácová M. Molecules 10 (2005) 937-960
12. Harnisch H. Liebigs Ann. Chem. 765 (1972) 8-14
13. Nohara A., Umetani T., and Sanno Y. Tetrahedron Lett. (1973) 1995-1998
14. Nohara A., Umetani T., and Sanno Y. Tetrahedron 30 (1974) 3553-3561
15. Nohara A. Tetrahedron Lett. (1974) 1187-1190
16. Klutchko S., Cohen M.P., Shavel J., and von Strandtmann M. J. Heterocycl. Chem. 11 (1974) 183-188
17. Petersen U., and Heitzer H. Liebigs Ann. Chem. (1976) 1659-1662
18. Hagen, H.; Nilz, G.; Walter, H.; Landes, A.; Freund, W. DE Patent 4039281, 1992; Chem. Abstr. 1992, 117, 111473k.
19. Reddy G.J., Latha D., Thirupathaiah C., and Rao K.S. Tetrahedron Lett. 45 (2004) 847-848
20. Nohara A., Ishiguro T., Ukawa K., Sugihara H., Maki Y., and Sanno Y. J. Med. Chem. 28 (1985) 559-568
21. Ghosh C.K., and Karak S.K. J. Heterocycl. Chem. 42 (2005) 1035-1042
22. Sosnovskikh V.Ya. Uspekhi Khim. 72 (2003) 550-578 Russ. Chem. Rev. 2003, 72, 489-516
23. Sosnovskikh V.Ya., Moshkin V.S., and Kodess M.I. Tetrahedron 64 (2008) 7877-7889
24. Ghosh C.K., SinhaRoy D.K., and Mukhopadhyay K.K. J. Chem. Soc., Perkin Trans. 1 (1979) 1964-1968
25. Jerzmanowska Z., Basiński W., and Zielińska L. Pol. J. Chem. 54 (1980) 383-386
26. Basiński W., and Jerzmanowska Z. Pol. J. Chem. 57 (1983) 471-481
27. Brown, R. E.; Lustgarten, D. M. U.S. Patent 3,932,466, 1976; Chem. Abstr. 1976, 84, 135471j.
28. Brown, R. E.; Lustgarten, D. M. U.S. Patent 4,024,160, 1977; Chem. Abstr. 1977, 87, 84821a.
29. Bevan P.S., Ellis G.P., Hudson H.V., and Romney-Alexander T.M. J. Chem. Soc., Perkin Trans. 1 (1986) 1643-1649
30. Nohara, A.; Sugihara, H.; Ukawa, K. Japan Patent 53111071, 1978; Chem. Abstr. 1979, 90, 54827.
31. 3: S{cyrillic}, 59.41; N{cyrillic}, 2.99; N, 13.86. Found: S{cyrillic}, 59.25; N{cyrillic}, 2.90; N, 13.74.
32. 2O: S{cyrillic}, 57.56; N{cyrillic}, 4.11; N, 13.42. Found: S{cyrillic}, 57.39; N{cyrillic}, 3.80; N, 13.04.
33. Checchi S., Pecori Vettori L., and Vincieri F. Gazz. Chim. Ital. 98 (1968) 1488-1502
34. Kaljaj V., Trkovnik M., and Stefanovic-Kaljaj L. J. Serb. Chem. Soc. 52 (1987) 183-185 Chem. Abstr. 1988, 108, 150410w
35. Elguero J. In: Katritzky A.R., Rees C.W., and Scriven E.F.V. (Eds). Comprehensive Heterocyclic Chemistry II Vol. 3 (1996), Pergamon, Oxford 18
36. Chantegrel B., Nadi A.I., and Gelin S. J. Org. Chem. 49 (1984) 4419-4424
37. Chantegrel B., Nadi A.I., and Gelin S. Tetrahedron Lett. 24 (1983) 381-384
38. Darbarwar M., and Sundaramurthy V. Synthesis (1982) 337-388