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Synthesis 2003(16): 2559-2563  
DOI: 10.1055/s-2003-42414
PAPER
© Georg Thieme Verlag Stuttgart · New York

A Novel Route to 1,2,3-Thiadiazole, 1,3,4-Thiadiazine, and 1,2,5-Triazepine Derivatives

Barbara Zaleska*a, Bartosz Trzewika, Jacek Grochowskib, Paweł Serdab
a Department of Organic Chemistry, Jagiellonian University, ul. Romana Ingardena 3, 30-060 Kraków, Poland
Fax: 48(12)6340515; e-Mail: zaleska@chemia.uj.edu.pl;
b Regional Laboratory of Physicochemical Analyses and Structural Research, ul. Romana Ingardena 3, 30-060 Kraków, Poland
Further Information

Publication History

Received 3 July 2003
Publication Date:
29 September 2003 (online)

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Abstract

New convenient methods for the synthesis of 1,2,3-thiadiazole, 1,3,4-thiadiazine, and 1,2,5-triazepine derivatives are reported. In the heterocyclization process, the reactivity of 1-thia-4-aza-1,3-butadiene system of syn-2-phenylhydrazono-3-oxothiobutanoic acid anilides was exploited.

Key words

ring closure - heterocycles - cyclizations - thiadiazole - thiadiazine - triazepine

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Compound 2a crystallizes in the monoclinic system. See experimental for details of X-ray structure determination. The structural data have been deposited at the Cambridge Crystallographic Data Centre under the reference number CCDC 209483.