Journal
TETRAHEDRON
Volume 64, Issue 51, Pages 11594-11602Publisher
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.tet.2008.10.026
Keywords
Benzothiazole; Amidine; Pinner reaction; Disulfide; Thiolate
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Funding
- Ministry of Science, Education and Sports of the Republic of Croatia [125-0982464-1356, 117-0000000-3283, 119-1191342-1339]
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The efficient synthesis of new amidino, N-isopropylamidino, 2-imidazolinyl substituted benzothiazoles and 2-aminothiophenoles by the Pinner reaction is described. The novel ring opening of benzothiazole with ammonia and ethylenediamine was found, and a plausible reaction mechanism proposed. The ring opening with ethylenediamine is selective and applicable to compounds bearing hydrolytically and amonolytically unstable substituents. Different amidino-substituted 2-aminothiophenoles were isolated in zwitterionic and disulfide form and their structures were determined by X-ray crystal structure analysis. (C) 2008 Elsevier Ltd. All rights reserved.
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