Journal
TETRAHEDRON LETTERS
Volume 52, Issue 5, Pages 592-594Publisher
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.tetlet.2010.11.136
Keywords
Ring expansion; Medium-sized ring; 1,5-Benzothiazocines; DMAD; NMR; X-ray crystallography
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Funding
- Hungarian Scientific Research Foundation (OTKA)
- European Union
- European Social Fund [TAMOP 4.2.1./B-09/KMR-2010-0003]
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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. (C) 2010 Elsevier Ltd. All rights reserved.
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