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Synthesis 2002(12): 1646-1648
DOI: 10.1055/s-2002-33636
SHORTPAPER
© Georg Thieme Verlag Stuttgart · New York

Synthesis of N-Substituted Thiazolidines and Dihydrobenzothiazoles

Alan R. Katritzky*, Sandeep K. Singh, Hai-Ying He
Center for Heterocyclic Compounds, Department of Chemistry, University of Florida, Gainesville, FL 32611-7200, USA
Fax: +1(352)3929199; e-Mail: katritzky@chem.ufl.edu;
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Publication History

Received 15 January 2002
Publication Date:
05 September 2002 (online)

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Abstract

Ethyl (4R)-3-(1H-1,2,3-benzotriazol-1-ylmethyl)-1,3-thiazolane-4-carboxylate (6) and 1-[1,3-benzothiazol-3(2H)-ylmethyl]-1H-1,2,3-benzotriazole (8) were readily prepared by reactions of l-cysteine ethyl ester hydrochloride and 1-aminothiophenol with benzotriazole and formaldehyde, respectively. Chiral thiazolidine esters 7a-c were obtained by reactions of intermediate 6 with organozinc derivatives. Nucleophilic substitutions of 8 with Grignard reagents gave N-substituted dihydrobenzothiazoles 9a-c.

Key words

benzotriazole - thiazolidine - dihydrobenzothiazole - cyclocondensation - organozinc reagent

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