The University of Southampton
University of Southampton Institutional Repository

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.

Full text not available from this repository.

More information

Published date: 2006

Identifiers

Local EPrints ID: 44416
URI: https://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

Catalogue record

Date deposited: 07 Mar 2007
Last modified: 14 Mar 2019 01:48

Export record

Download statistics

Downloads from ePrints over the past year. Other digital versions may also be available to download e.g. from the publisher's website.

View more statistics

Atom RSS 1.0 RSS 2.0

Contact ePrints Soton: eprints@soton.ac.uk

ePrints Soton supports OAI 2.0 with a base URL of https://eprints.soton.ac.uk/cgi/oai2

This repository has been built using EPrints software, developed at the University of Southampton, but available to everyone to use.

We use cookies to ensure that we give you the best experience on our website. If you continue without changing your settings, we will assume that you are happy to receive cookies on the University of Southampton website.

×