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Isomerization in the Oxidative Cyclocondensation of 2-Aroylmethyl-1H-benzimidazoles with o-Aminothiophenol

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Abstract

Oxidative cyclocondensation of 2-aroylmethyl-1H-benzimidazoles with o-aminothiophenol gave the previously unknown 3-aryl-2-(2-benzimidazolyl)-4H-1,4-benzothiazines and (or) the isomeric 2H-1,4-benzothiazines. 2-(4-Nitrophenacyl)-1H-benzimidazole and 2-phenacylbenzothiazole gave 4H-1,4-benzothiazines which are not liable to isomerize but the reaction of the first compound is complicated by a hydrolytic fission which yields 2-[2-(4-nitrobenzoylamino)phenylthiomethyl]benzimidazole. A mixture of dimethylsulfoxide, acetic acid, and water was used as oxidant and solvent. The effect of the substituent and of the solvent on the tendency of the products to undergo prototropic isomerization in the benzothiazine ring have been studied.

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Authors and Affiliations

  1. Institute of Organic Chemistry, National Academy of Sciences of Ukraine, Kiev, 02094

    I. B. Dzvinchuk, A. V. Vypirailenko & M. O. Lozinskii

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  1. I. B. Dzvinchuk
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  2. A. V. Vypirailenko
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  3. M. O. Lozinskii
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Dzvinchuk, I.B., Vypirailenko, A.V. & Lozinskii, M.O. Isomerization in the Oxidative Cyclocondensation of 2-Aroylmethyl-1H-benzimidazoles with o-Aminothiophenol. Chemistry of Heterocyclic Compounds 40, 1199–1206 (2004). https://doi.org/10.1023/B:COHC.0000048295.31636.0d

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  • DOI: https://doi.org/10.1023/B:COHC.0000048295.31636.0d

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