On the reaction of 3-cyanochromones with phenyl- and methylhydrazines: Structural revision and a simple synthesis of chromeno[4,3-c]pyrazol-4-ones

Journal of Heterocyclic Chemistry

Volumn 47, Issue 3, 2010, Pages 629-633

  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

[No Author keywords available]

Indexed keywords

1 PHENYLCHROMENO[ 4,3 C]PYRAZOL 4 (1H) ONE; 2 AMINOCHROMONE 3 CARBALDEHYDE; 2 METHYLCHROMENO[ 4,3 C]PYRAZOL 4 (2H) ONE; 3 ( 2 HYDROXYARYL) 1 METHYLPYRAZOLE 4 CARBONITRILE; ALDEHYDE DERIVATIVE; CHROMONE DERIVATIVE; METHYLHYDRAZINE DERIVATIVE; PHENYLHYDRAZINE; PHENYLHYDRAZINE DERIVATIVE; PHENYLHYDRAZONE DERIVATIVE; PYRAZOLE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; BIOTRANSFORMATION; CHEMICAL REACTION; CRYSTAL STRUCTURE; CYCLIZATION; CYCLOADDITION; HETEROCYCLIZATION; POLYMERIZATION; RING OPENING; STEREOCHEMISTRY; SYNTHESIS;

EID: 77953004721     PISSN: 0022152X     EISSN: 19435193     Source Type: Journal    
DOI: 10.1002/jhet.370     Document Type: Article

References (27)

1. (a) Harnisch, H. Justus Liebigs Ann Chem 1972, 765, 8;
2. (b) Nohara, A.; Umetani, T.; Sanno, Y. Tetrahedron Lett 1973, 1995;
3. (c) Nohara, A.; Umetani, T.; Sanno, Y. Tetrahedron 1974, 30, 3553.
4. (a) Nohara, A. Tetrahedron Lett 1974, 1187;
5. (b) Klutchko, S.; Cohen, M. P.; Shavel, J.; von Strandtmann, M. J Heterocycl Chem 1974, 11, 183.
6. (a) Petersen, U.; Heitzer, H. Justus Liebigs Ann Chem 1976, 1659;
7. (b) Hagen, H.; Nilz, G.; Walter, H.; Landes, A.; Freund, W. D.E. Pat. 4,039,281, (1992);
8. Chem Abstr 1992, 117, 111473.
9. Reddy, G. J.; Latha, D.; Thirupathaiah, C.; Rao, K. S. Tetrahedron Lett 2004, 45, 847.
10. Hsung, R. P.; Zificsak, C. A.; Wei, L.-L.; Zehnder, L. R.; Park, F.; Kim, M.; Tran, T.-T. T. J Org Chem 1999, 64, 8736.
11. Ghosh, C. K.; Karak, S. K. J Heterocycl Chem 2005, 42, 1035.
12. Nohara, A.; Ishiguro, T.; Ukawa, K.; Sugihara, H.; Maki, Y.; Sanno, Y. J Med Chem 1985, 28, 559.
13. (a) Ghosh, C. K.; Tewari, N.; Bandyopadhyay, C. Indian J Chem 1983, 22B, 1200;
14. (b) Ghosh, C. K.; Ghosh, C.; Patra, A. Indian J Chem 1998, 37B, 387.
15. Ghosh, C. K.; SinhaRoy, D. K.; Mukhopadhyay, K. K. J Chem Soc Perkin Trans 1 1979, 1964.
16. Sosnovskikh, V. Ya.; Moshkin, V. S.; Kodess, M. I. Tetrahedron Lett 2008, 49, 6856.
17. (a) Colotta, V.; Cecchi, L.; Melani, F.; Palazzino, G.; Filacchioni, G. Tetrahedron Lett 1987, 28, 5165.
18. Ghosh, C. K.; Pal, C. Indian J Chem 1985, 24B, 1288.
19. Chantegrel, B.; Nadi, A.-I.; Gelin, S. Tetrahedron Lett 1983, 24, 381.
20. (a) Moorty, S. R.; Sundaramurthy, V.; Subba Rao, N. V. Indian J Chem 1973, 11, 854;
21. (b) Strakova, I.; Petrova, M.; Belyakov, S.; Strakovs, A. Chem Heterocycl Comp 2003, 39, 1608.
22. Steinführer, T.; Hantschmann, A.; Pietsch, M.; Weißenfels, M. Justus Liebigs Ann Chem 1992, 23.
23. Nohara, A.; Kuriki, H.; Saijo, T.; Sugihara, H.; Kanno, M.; Sanno, Y. J Med Chem 1977, 20, 141.
24. Trimeche, B.; Gharbi, R.; Houla, S. E.; Martin, M.-T.; Nuzillard, J. M.; Mighri, Z. J Chem Res 2004, 170.
25. (a) Darbarwar, M.; Sundaramurthy, V. Synthesis 1982, 337;
26. (b) Colotta, V.; Cecchi, L.; Filacchioni, G.; Melani, F.; Palazzino, G.; Martini, C.; Giannaccini, G.; Lucacchini, A. J Med Chem 1988, 31, 1;
27. (c) Ibrahim, M. A.ARKIVOC 2008, xvii, 192.