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Free Content 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

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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 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.

Keywords: 1,4-BENZOTHIAZINES, O-AMINOBENZENETHIOLS, CRYSTAL STRUCTURES, β-KETOESTERS, 1,3-DIONES

Document Type: Research Article

DOI: https://doi.org/10.3184/030823406777980709

Publication date: 2006-07-01

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  • The Journal of Chemical Research is a monthly journal which has a broad international authorship and publishes research papers and reviews in all branches of experimental chemistry.

    Established in 1977 as a joint venture by the British, French and German chemical societies it maintains the high standards set by the founding societies. Each paper is independently peer reviewed and only carefully evaluated contributions are accepted.

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

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