Cycloaddition reactions of 1,3-benzothiazines—I. : Reactions of 2-phenyl-4-H and 4-phenyl-2H-1,3-benzothiazine derivatives with substituted acetyl chlorides |
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Authors: | L Fodor J Szabó P Sohár |
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Institution: | Institute of Pharmaceutical Chemistry, University Medical School, H-6701 Szeged,P.O.B. 121, Hungary;“EGYT” Pharmacochemical Works, H-1475 Budapest P.O.B. 100, Hungary |
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Abstract: | 6,7-Dimethoxy-2-phenyl-4-1,3-benzothiazine (1) and 6,7-dimethoxy-4-phenyl-2-1,3-benzothiazine (2) react with substituted acetyl chlorides to give linearly, and new angularly condensed β-lactam derivatives (4,5). Heating of the latter compounds with hydrogen chloride in anhydrous ethanol leads to the formation of the corresponding 4- and 2-1,3-benzothiazinium chloride, respectively. The configurations of these compounds (the mutual positions of the substituents relative to the β-lactam ring) were determined by 1H and 13C studies, also making use of the aromatic solvent-induced shifts. |
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