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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

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
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
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.
0308-2342
445-448
Dandia, A.
95715e0b-d86d-4a0f-93b3-cbacf8dccedb
Sarawgi, P.
76c914a2-4563-4900-bb34-6dbd5e04f703
Hursthouse, M.B.
57a2ddf9-b1b3-4f38-bfe9-ef2f526388da
Bingham, A.L.
8349446d-f3ab-4a2c-9b7b-88b01a9f59c0
Light, M.E.
cf57314e-6856-491b-a8d2-2dffc452e161
Drake, J.E.
cf5a2c45-a2cb-4361-8b31-f2295e2050b7
Ratnani, R.
5c33e340-5b43-4fae-b43d-c37ae26100ff
Dandia, A.
95715e0b-d86d-4a0f-93b3-cbacf8dccedb
Sarawgi, P.
76c914a2-4563-4900-bb34-6dbd5e04f703
Hursthouse, M.B.
57a2ddf9-b1b3-4f38-bfe9-ef2f526388da
Bingham, A.L.
8349446d-f3ab-4a2c-9b7b-88b01a9f59c0
Light, M.E.
cf57314e-6856-491b-a8d2-2dffc452e161
Drake, J.E.
cf5a2c45-a2cb-4361-8b31-f2295e2050b7
Ratnani, R.
5c33e340-5b43-4fae-b43d-c37ae26100ff

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), 445-448.

Record type: Article

Abstract

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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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: 08 Jan 2022 02:49

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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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