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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

Record type: Article

The reaction between 2-aminobenzenethiol and ethyl acetoacetate is studied under a variety of conditions, and a procedure for the exclusive synthesis of 1,4-benzothiazines by the neat reaction of substituted aminothiols with beta-ketoesters and beta-dicarbonyl compounds in 85-96% yield is described. With microwave heating, even when both the reactants are solid, yields are high, reaction times brief, and work-up easy. A facile reaction is also observed even in a solid-state reaction. The molecular structure of ethyl 7-chloro-3-methyl-4H-1,4-benzothiazine-2-carboxylate (4d) was determined by single-crystal X-ray diffraction.

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Citation

Dandia, A., Sarawgi, P., Hursthouse, M.B., Bingham, A.L., Light, M.E., Drake, J.E. and Ratnani, R. (2006) 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, (7), pp. 445-448.

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Published date: 2006

Identifiers

Local EPrints ID: 44416
URI: http://eprints.soton.ac.uk/id/eprint/44416
ISSN: 0308-2342
PURE UUID: 162e825a-9413-4de1-9234-bdbd4932fb76
ORCID for M.E. Light: ORCID iD orcid.org/0000-0002-0585-0843

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Date deposited: 07 Mar 2007
Last modified: 17 Jul 2017 15:14

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Contributors

Author: A. Dandia
Author: P. Sarawgi
Author: M.B. Hursthouse
Author: A.L. Bingham
Author: M.E. Light ORCID iD
Author: J.E. Drake
Author: R. Ratnani

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