Abstract
8-Chloro-5-methoxy/8-chloro-4H-1,4-benzothiazines were synthesized by condensation followed by oxidative cyclisation of 2-amino-6-chloro-3-methoxy/2-amino-3-chlorobenzenethiol with β–diketones/β–ketoesters in the presence of dimethyl sulphoxide. By treating 4H-1,4-benzothiazines with 30% hydrogen peroxide in glacial acetic acid, 4H-1,4-benzothiazine-1,1-dioxides (sulphones) were synthesized. The 4H-1,4-benzothiazines have also been used as a base to prepare ribofuranosides by the reaction with β–D-ribofuranose-1-acetate-2,3,5-tribenzoate. All the synthesized compounds have been characterized by spectral and elemental analysis and have been examined for antimicrobial and anthelmintic activity.
4H-1,4-benzothiazines, the nitrogen and sulphur containing heterocycles are prepared by condensation followed by oxidative cyclization of 2-aminobenzenethiols with β-diketones/β-ketoester in dimethylsulphoxide. These compounds were then used as base to prepare ribofuranosides and their sulphones.
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Acknowledgements
The authors are thankful to the Department of Chemistry, University of Rajasthan, Jaipur, for providing laboratory facilities and spectral data analysis. Authors are also thankful to Rajiv Academy for Pharmacy, Mathura for assistance in carrying out the biological activities. The University Grants Commission (UGC), New Delhi is duly acknowledged for financial support through Major Research Project and UGC Research Award Scheme.
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KHANDELWAL, N., ABHILASHA, GAUTAM, N. et al. An efficient synthesis and biological study of substituted 8-chloro-5-methoxy/8-chloro-4H-1,4-benzothiazines, their sulphones and ribofuranosides. J Chem Sci 125, 85–93 (2013). https://doi.org/10.1007/s12039-013-0363-4
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DOI: https://doi.org/10.1007/s12039-013-0363-4