An efficient procedure for the preparation of 4-methyl-2-thiocoumarins by the reaction of 4-methylcoumarins with lawesson's reagent

Journal of Heterocyclic Chemistry

Volumn 42, Issue 4, 2005, Pages 739-742

  Lévai, Albert ^a   Jeko, József ^b  

^a UNIVERSITY OF DEBRECEN   (Hungary)

^b ICN Hungary Co Ltd   (Hungary)

Author keywords

[No Author keywords available]

Indexed keywords

4 METHYL 2 THIOCOUMARIN DERIVATIVE; 4 METHYL 7 (2 METHYLBENZYLOXY) 2 THIOCOUMARIN; 4 METHYL 7 (2 METHYLBENZYLOXY)COUMARIN; 4 METHYL 7 (3 METHYLBENZYLOXY) 2 THIOCOUMARIN; 4 METHYL 7 (3 METHYLBENZYLOXY)COUMARIN; 4 METHYL 7 (4 METHYLBENZYLOXY)COUMARIN; 4 METHYL 7 (4 NITROBENZYLOXY) 2 THIOCOUMARIN; 4 METHYL 7 (4 NITROBENZYLOXY)COUMARIN; 4 METHYL 7 TOSYLOXY 2 THIOCOUMARIN; 7 (2 CHLOROBENZYLOXY) 4 METHYL 2 THIOCOUMARIN; 7 (2 CHLOROBENZYLOXY) 4 METHYLCOUMARIN; 7 (2 FLUORBENZYLOXY) 4 METHYL 2 THIOCOUMARIN; 7 (2 FLUOROBENZYLOXY) 4 METHYLCOUMARIN; 7 (3 FLUORBENZYLOXY) 4 METHYL 2 THIOCOUMARIN; 7 (3 FLUOROBENZYLOXY) 4 METHYLCOUMARIN; 7 (4 CHLOROBENZYLOXY) 4 METHYL 2 THIOCOUMARIN; 7 (4 CHLOROBENZYLOXY) 4 METHYLCOUMARIN; 7 (4 FLUORBENZYLOXY) 4 METHYL 2 THIOCOUMARIN; 7 (4 FLUOROBENZYLOXY) 4 METHYLCOUMARIN; 7 BENZENESULFONYLOXY 4 METHYL 2 THIOCOUMARIN; 7 BENZYLOXY 4 METHYL 2 THIOCOUMARIN; COUMARIN DERIVATIVE; HYMECROMONE; LAWESSON REAGENT; REAGENT; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL REACTION; CHEMICAL STRUCTURE; DRUG SYNTHESIS; KOENIGS KNORR REACTION; STRUCTURE ACTIVITY RELATION;

EID: 19644374542     PISSN: 0022152X     EISSN: None     Source Type: Journal    
DOI: 10.1002/jhet.5570420443     Document Type: Article

References (24)

1. H. von Pechmann and C. Duisberg, Ber. Dtsch. Chem. Ges., 16, 2119 (1883).
2. H. von Pechmann and O. Schwarz, Ber. Dtsch. Chem. Ges., 32, 3696 (1899).
3. H. von Pechmann and E. Hanke, Ber. Dtsch. Chem. Ges., 34, 354 (1901).
4. J. J. Drysdale, H. B. Stevenson and W. H. Sharkey, J. Am. Chem. Soc., 81, 4908 (1959).
5. R. T. Taylor and R. A. Cassell, Synthesis, 672 (1982).
6. T. Inaba, T. Ohgushi, Y. Iga and E. Hasegawa, Chem. Pharm. Bull., 32, 1597 (1984).
7. Q. Wang, M. Wolff, T. Polat, Y. Du and R. J. Linhardt, Bioorg. Med. Chem. Lett., 10, 941 (2000).
8. M. Bilban, A. Billich, M. Auer and P. Nussbaumer, Bioorg. Med. Chem. Lett., 10, 967 (2000).
9. P. R. Bonneau, F. Hasani, C. Plouffe, E. Malenfant, S. R. LaPlante, I. Guse, W. W. Ogilvie, R. Plante, W. C. Dawidson, J. L. Hopkins, M. M. Morelock, M. G. Cordingley and R. Déziel, J. Am. Chem. Soc., 121, 2965 (1999).
10. C. Gnerre, M. Catto, F. Leonetti, P. Weber, P-A. Carrupt, C. Altomare, A. Carotti and B. Testa, J. Med. Chem., 43, 4747 (2000).
11. N. L. Maidwell, M. R. Rezai, C. A. Roeschlaub and P. G. Sammes, J. Chem. Soc. Perkin Trans. 1, 1541 (2000).
12. S. Chimichi, M. Boccalini and B. Cosimelli, Tetrahedron, 58, 4851 (2002).
13. F. M. Dean, J. Goodchild and A. W. Hill, J. Chem. Soc. C, 2192 (1969).
14. H. Nakazumi and T. Kitao, Bull. Chem. Soc. Jpn., 52, 160 (1979).
15. B. S. Pedersen, S. Scheibye, N. H. Nilsson and S. O. Lawesson, Bull. Chem. Soc. Belges, 87, 223 (1978).
16. A. Lévai, J. Chem. Research (S), 163 (1992).
17. A. Lévai and Z. Szabó, Bull.Chim. Soc. Fr., 128, 976 (1991).
18. A. Lévai and Z. Szabó, J. Chem. Research (S), 380 (1992).
19. A. Lévai, T. Tímár, L. Frank and S. Hosztafi, Heterocycles, 34, 1523 (1992).
20. A. Lévai and Z. Bálint, Arch. Pharm. (Weinheim), 326, 73 (1993).
21. G. Tóth, J. Halász, A. Lévai and B. Rezessy, Monatsh. Chem., 128, 625 (1997).
22. A. Lévai, Arch. Pharm. (Weinheim), 325, 721 (1992).
23. A. A. Shamshurin and R. A. Ibadulin, Trudy Uzbekskogo Gosudarst. Univ., 1 (1941);
24. Chem. Abstr., 35, 37638 (1941).