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

Authors: Dandia, Anshu; Dandia, Anshu; Sarawgi, Pritima; Sarawgi, Pritima; Hursthouse, Michael B.; Hursthouse, Michael B.; Bingham, Ann L.; Bingham, Ann L.; Light, Mark E.; Light, Mark E.; Drake, John E.; Drake, John E.; Ratnani, Raju; Ratnani, Raju

Source: Journal of Chemical Research, Volume 2006, Number 7, 1 July 2006 , pp. 445-448(4)

Publisher: Science Reviews 2000 Ltd

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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 β-ketoesters and β-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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    Recent papers have described new synthetic methods, new heterocyclic compounds, new natural products, and the inorganic chemistry of metal complexes.

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