Journal
PHOSPHORUS SULFUR AND SILICON AND THE RELATED ELEMENTS
Volume 191, Issue 2, Pages 220-229Publisher
TAYLOR & FRANCIS LTD
DOI: 10.1080/10426507.2015.1072191
Keywords
Three-component reaction; 1,3-thiazine; Staudinger reaction; beta-lactam-condensed; 1,3-thiazine; 1,4-thiazepine
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Funding
- Centre National de la Recherche Scientifique (CNRS)
- Region Basse-Normandie
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Variously substituted 1,3-thiazines have been prepared by a three-component reaction involving a thioamide, an aldehyde, and an alkene. Two diastereomeric thiazines were transformed by stereoselective Staudinger reaction into the corresponding chloro--lactam-condensed-1,3-thiazines, and one of them was rearranged in basic media to afford a highly substituted 1,4-thiazepine. Several of the obtained compounds (six 1,3-thiazines and one -lactam-condensed-1,3-thiazine) were analyzed by X-ray crystallography, which enabled to assign their spatial arrangement and stereochemistry.
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