Arylthioureas with bromine or its equivalents gives no ‘Hugerschoff’ reaction product

Yella, Ramesh ; Murru, Siva ; Ali, Abdur Rezzak ; Patel, Bhisma K. (2010) Arylthioureas with bromine or its equivalents gives no ‘Hugerschoff’ reaction product Organic & Biomolecular Chemistry, 8 (15). pp. 3389-3393. ISSN 1477-0520

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Official URL: http://pubs.rsc.org/en/Content/ArticleLanding/2010...

Related URL: http://dx.doi.org/10.1039/C003892J

Abstract

The in situ generated aryl–alkyl unsymmetrical thiourea obtained by the reaction of an aryl isothiocyanate with an aliphatic secondary amine on treatment with bromine or its equivalent gave exclusively a product having a thioamido guanidino moiety and not the expected Hugerschoff product 2-aminobenzothiazole. A plausible reaction mechanism has been proposed for this unprecedented transformation and the scope has been extended to various substrates.

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