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Ring Transformations of 1,3 -Benzothiazines, 51 synthesis of benzisothiazoles by the oxidative ring contraction of 2-aryl-4H-and 4-ARYL-2H-1,3-benzothiazines

✍ Scribed by Ja´nos Szabo´; Erzse´bet Szu¨cs; Lajos Fodor; A´gnes Kato´cs; Gabor Bernath; Pal Sohar

Publisher
Elsevier Science
Year
1988
Tongue
French
Weight
662 KB
Volume
44
Category
Article
ISSN
0040-4020

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✦ Synopsis

6,7-Dimethoxy-2-phenyl-4H-l,3-benzothiazine (la) was oxidized with hydrogen peroxide to yield [2,2'-bis(benzoyIaminomethyl)-4,4',5,5'-tetramethoxyldiphenyl disulfide (2). Potassium permanganate oxidation of Aa gave 6,7-dimethoxy-2-phenyl-4B-1,3benzothiazinll-one (5a), wKch was oxidized with the calculated amounts of perbenzobenzothiazines (13a-f), resulting -\_in the formation of 3-arfi-5,6-dialkoxy-l,2-ben~~s~thiazoles (T&-f). The assumed mechanism of these ring transformations is d%?cbenzothiazines to 1,2-benzisothiazoles actually represents a ring transformation reaction of 1,3-benzothiaxines and a new synthesis of 1,2-benzisothiazole derivatives. The structures of the new compounds were confirmed by ir, 'H and'3C nmr spectroscopy.

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