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Expected and unexpected reactions of 1,3-benzothiazine derivatives, II. Formation of isomeric 5,6-dihydro-1,5-benzothiazocines

✍ Scribed by Lajos Fodor; Péter Csomós; Antal Csámpai; Pál Sohár; Tamás Holczbauer; Alajos Kálmán

Book ID: 104098686
Publisher: Elsevier Science
Year: 2011
Tongue: French
Weight: 335 KB
Volume: 52
Category: Article
ISSN: 0040-4039
DOI: 10.1016/j.tetlet.2010.11.136

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✦ Synopsis

A method for the synthesis of medium-sized 1,5-benzothiazocines by ring enlargement of 1,3-benzothiazines has been developed. When N-alkyl-1,3-benzothiazines were reacted with dimethyl acetylenedicarboxylate in acetonitrile at room temperature, regioisomeric 5,6-dihydro-2H-1,5-benzothiazocines and 5,6-dihydro-4H-1,5-benzothiazocines were obtained as novel ring systems. Dimethyl acetylenedicarboxylate could attack either the nitrogen or the sulfur atom of the thiazines. NMR spectroscopic and X-ray crystallographic investigations confirmed the structures of the products.

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