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Synthesis, reactions, and biological activity of 1,4-benzothiazine derivatives

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Abstract

6,7-Dimethoxy-2H-1,4-benzothiazin-3(4H)-one reacts with dimethylformamide dimethylacetal (DMF-DMA) to give the novel enaminone 2-(dimethylaminomethylene)-6,7-dimethoxy-2H-1,4-benzothiazin-3(4H)-one. The reaction of the latter with various active methylene compounds afforded pyrido[3,2-b][1,4]benzothiazines. Also, coupling of the enaminone with diazotized aniline derivatives gave 2-(arylhydrazono)-6,7-dimethoxy-2H-1,4-benzothiazin-3(4H)-ones. Spectral data indicated that the latter compounds exist predominantly in the hydrazone tautomeric form. In addition, coupling of the enaminone with diazotized heterocyclic amines afforded tetra- and pentaheterocyclic ring systems. The antitumor and antimicrobial activity of some of the synthesized compounds was screened.

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Authors and Affiliations

  1. Department of Chemistry of Natural and Microbial Products, National Research Center, Dokki, Cairo, Egypt

    Eman M. H. Abbas

  2. Department of Chemistry, Faculty of Science, University of Cairo, Giza, Egypt

    Thoraya A. Farghaly

Authors
  1. Eman M. H. Abbas
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  2. Thoraya A. Farghaly
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Correspondence to Thoraya A. Farghaly.

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Abbas, E.M.H., Farghaly, T.A. Synthesis, reactions, and biological activity of 1,4-benzothiazine derivatives. Monatsh Chem 141, 661–667 (2010). https://doi.org/10.1007/s00706-010-0312-6

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  • DOI: https://doi.org/10.1007/s00706-010-0312-6

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