Synthesis of (Z)-hetarylmethylene and (Z)-substituted benzylidene derivatives of 4H-benzo[1,4]thiazine-3-thiones and their subsequent conversion to benzothiopyrano-[3,2-b][1,4]benzothiazines

Arkivoc

Volumn 2006, Issue 2, 2006, Pages 1-14

  Kamila, Sukanta ^a   Koh, Benjamin ^a   Zhang, Hongming ^a   Biehl, Edward R ^a  

^a SOUTHERN METHODIST UNIVERSITY   (United States)

Author keywords

(Z) (hetarylmethylene 2 yl) 4H benzo 1,4 thiazine 3 thiones; 3,4 dimethoxybenzyne; Benzothiopyrano 3,2 b 1,4 benzothiazines; Cycloaddition; Diels Alder; Dimethyl acetylenedicarboxylate

Indexed keywords

EID: 34247358297     PISSN: None     EISSN: 14246376     Source Type: Journal    
DOI: None     Document Type: Article

References (25)

1. For selected reports on the biological activities of nitrogen-sulfur heterocycles see: (a) Sing, S. P.; Parmar, S. S.; Raman, K.; Stenberg, V. I. Chem. Rev. 1981, 81, 175.
2. (b) Hanefeld, W.; Schlitzer, M. J. Heterocyclic. Chem. 1995, 32, 1019.
3. (c) Gupta, R. R.; Ojha, K. G. Phenothiazine and 1,4-Benzothiazines, Chemical and Biochemical Aspects; Elsevier: Amsterdam, 1988; Vol. 4, Issue No 2 pp-163-260.
4. (d) Grandolini, G. Ambrogi, V.; Rossi, C.; Tiralti, M. C.; TuHobello, L. Eur. J. Med. Chem. 1986, 21, 455.
5. (e) Gupta, R. R.; Dev, P. K.; Sharma, M. L.; Rajoria, C. M.; Gupta, A.; Nayati, M. Anti-Cancer Drugs. 1993, 4, 589.
6. (f) Todorow, D. K.; Ilavionova, M. V.; Gupta, R. R.; Molnar, J.; Motohashi, N. Heterocycl. Commun. 1995, 1, 153.
7. Sathunuru, R.; Biehl, E. Arkivoc 2004 (xiv) 51.
8. Sathunuru, R.; Zhang, H.; Rees, C. W.; Biehl, E. Heterocycles 2005, 65, 161
9. Rao, U. N.; Sathunuru, R.; Biehl, E. R. Heterocycles 2004, 63, 1067.
10. Kitamura, T.; Yamane, M.; Inoue, K.; Todaka, M.; Fukatsu, N.; Meng, Z.; Fujiwara, Y. J. Am. Chem. Soc. 1999, 121, 11674.
11. Pena, D.; Perez, D.; Guitan, F.; Castedo, L. J. Am. Chem. Soc.1999, 121, 5827.
12. Kamila, S.; Biehl, E. Heterocycles 2005, 63, 2785.
13. Kamila, S.; Zhang, H.; Zhu, D. Biehl, E. R. Heterocycles 2005, 65, 579.
14. Eggers, K.; Fyles, T. M.; Montoya-Pelaez, P. J. J. Org. Chem. 2001, 66, 2966.
15. Albuquerque, J. F. C.; Galdino, S. L.; Chantegrel, J.; Thomasson, F.; Pitta, I. R.; Luu-duc, C. Ann. Pharm. Fr. 1997, 55, 201.
16. Brandao, S. S. F.; Rocha-Filho, J. A.; Chantegrel, J.; Alburguegue, J. F. C.; Zimenes, E. A.; Galdino, S. L. Pitta, I. R.; Perrissin, M.; Luu-duc, C. Ann. Pharm Fr. 1997, 55, 206.
17. Mostoslawski, M. A.; Ismailski, W. A. Zh. Obsch. Khim 1961, 31, 17.
18. Steinle, W.; Ruck-Braun, K. J. Org. Chem. 2003, 5, 141.
19. Worley, J. W.; Ratts, K. W.; Cammack, K. L. J. Org. Chem. 1975, 40, 1731.
20. Matler, U. E.; Pascual. C.; Pretsch, E.; Pross, A.; Simon, W.; Sternhell, S. Tetrahedron, 1969, 25, 691.
21. Hart; H.; Oku, A. J. Org. Chem. 1972, 37, 4269.
22. Caliendo, G.; Gieco, E.; Perissutti, V.; Santugada, A.; Santini, S.; Albrizio, S.; Fattorusso, C.; Pinto, A.; Sorrentino, R. Eur. J. Med. Chem. 1998, 33, 957.
23. Morino, T.; Yamamoto, T. J. Chem. Eng. Jpn. 1997, 30, 1005.
24. Schwarz, I.; Stark, U.; Haiden, U.; Stark, G.; Tritthard, H. A. N-S Arch. Pharacol. 1995, 29, 471.
25. Rao, S. S.; Chowdary, K. S.; Prashant, A.; Krishnan, U. S. H. Synth. Commun. 2001, 31, 3469.