Synthesis of a series of 2,3-disubstituted 4H-1,4-benzothiazines and X-ray crystal structure of ethyl 7-chloro-3-methyl-4H-1,4-benzothiazine-2-carboxylate

Journal of Chemical Research

Volumn , Issue 7, 2006, Pages 445-448

  Dandia, Anshu ^a   Sarawgi, Pritima ^a   Hursthouse, Michael B ^b   Bingham, Ann L ^b   Light, Mark E ^b   Drake, John E ^c   Ratnani, Raju ^d  

^a UNIVERSITY OF RAJASTHAN   (India)

^b UNIVERSITY OF SOUTHAMPTON   (United Kingdom)

^c UNIVERSITY OF WINDSOR   (Canada)

^d M D S UNIVERSITY   (India)

Author keywords

1,3 diones; 1,4 benzothiazines; Crystal structures; o aminobenzenethiols; ketoesters

Indexed keywords

EID: 33747202989     PISSN: 03082342     EISSN: None     Source Type: Journal    
DOI: 10.3184/030823406777980709     Document Type: Article

References (39)

1. R.R. Gupta (ed.), Phenothiazines and 1,4-Benzothiazines: Chemical and Biomedical Aspects, Elsevier, Amsterdam, 1988.
2. C. Jaime, B. Arthur, D. Jose and G. Neira, J. Chem. Res., 2005, 27.
3. S.B. Munde, S.P. Bondge, V.E. Bhingalikar and R.A. Mane, Green Chem., 2003, 5, 278.
4. F. Chioccara, L. Oliva and G. Prota, Synthesis, 1978, 744.
5. F. Chioccara and G. Prota, Synthesis, 1977, 876.
6. I.B. Dzvinchuk, A.V. Vypirailenko and M.O. Lozinskii, Chem. Heterocyclic Compds, 2004, 40, 1199.
7. G. Liso, G. Trapani, A. Reho, A. Latrofa and F. Mortacchi, Synthesis, 1983, 755.
8. (a) A.I. Kiprianov and V.A. Portnyagina, Zhur. Obshch. Khim., 1955, 25, 2257;
9. Chem. Abstr. 1956, 50, 9378b;
10. (b) S. Miyano, N. Abe, K. Sumoto and K. Teramoto, J. Chem. Soc., Perkin Trans. 1, 1976, 1146.
11. (a) A.K. Gupta and U.C. Pant, Indian J. Chem., 1981, 20B, 157;
12. (b) W. Ried and W. Marx, Chem. Ber., 1957, 90, 2683.
13. (a) A.D. Hoz, A. Diaz-Ortiz and A. Moreno, Chem. Soc. Rev., 2005, 34, 164;
14. (b) M. Nüchter, B. Ondruschka, W. Bonrath and A. Gum, Green Chem., 2004, 6, 128;
15. (c) B.L. Hayes, Aldrichim. Acta, 2004, 37, 66;
16. (d) C.O. Kappe, Angew. Chem. Int. Ed., 2004, 43, 6250;
17. (e) C.O. Kappe, (Ed.), Mol. Diversity, 2003, 7, 95.
18. (a) A.D. Hoz, A. Diaz-Ortiz and A. Moreno, Curr. Org. Chem., 2004, 8, 903;
19. (b) A. Loupy, in Microwaves in Organic Synthesis, Wiley-VCH, Weinheim (Germany), 2002, ISBN 3-527-30514-9;
20. (c) P. Lidstrom, J. Tierney, B. Wathey and J. Westman, Tetrahedron, 2001, 57, 9225;
21. (d) R.S. Varma, Green Chemistry, 1999, 43, 1;
22. (e) A. Loupy and L. Perreux, Tetrahedron, 2001, 57, 9199.
23. (a) A. Dandia, M. Sati, K. Arya, P. Sarawgi and A. Loupy, Arkivoc, 2005 (i), 105;
24. (b) A. Dandia, K. Arya, M. Sati and S. Gautam, Tetrahedron, 2004, 60 5253;
25. (c) A. Dandia, M. Sati and A. Loupy, Green Chem., 2002, 4, 599;
26. (d) A. Dandia, M. Upreti, U.C. Pant, and B. Rani, J. Chem. Res. 1998,(S), 752,(M), 3348.
27. K.G. Nazarenko, N.A. Shtil, A.N. Chernega, M.O. Lozinskii and A.A. Tolmachev, Synthesis, 2004, 8, 1195.
28. A.V. Lesin, O. Ya. Borbulevych, S.V. Kurbatov, A.E. Ruzhnikov, M.Yu. Antipin and L.P. Olekhnovich, Russ. Chem. Bull., Internat. Ed., 2001, 50, 1264.
29. G. Ferguson and B. Ruhl, Cryst. Struct. Commun., 1982, 11, 1033.
30. (a) R.R. Gupta, G.S. Kalawania and R. Kumar, Bull. Chem. Soc. Japan, 1984, 57, 2343;
31. (b) R.R. Gupta, K.G.O. Jha, G.S. Kalawania and M. Kumar, Heterocycles, 1980, 14, 1145;
32. (c) Y. Maki, M. Suzuki and T. Yamada, Chem. Pharm. Bull., 1966, 14, 770,
33. Chem. Abstr., 1966, 65, 16962.
34. U.C. Pant, B.S. Gaur and M. Chugh, Indian J. Chem., 1987, 26B, 947.
35. A.J.M. Duisenberg, J. Appl. Cryst., 1992, 25, 92.
36. G.M. Sheldrick, SADABS V2. 2003, 10.
37. G.M. Sheldrick, Acta Cryst., 1990, A46, 467.
38. L.J. Farrugia, J. Appl. Cryst., 1999, 32, 837.
39. G.M. Sheldrick, SHELXL97, Structure Determination Software; University of Göttingen, Germany, 1997.