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The preparation of 2 H ‐1,2,3‐benzothiadiazine‐1,1‐dioxides, 11 H ‐11 a ‐dihydrobenzimidazo[1,2‐ b ] [1,2] benzisothiazole‐5,5‐dioxides, 6 H ‐dibenzo[ c,g ] [1,2,5] thiadiazocine‐5,5‐dioxides and 5 H ‐Dibenzo[ c,g ] [1,2,6] thiadiazocine‐6,6‐dioxides
Author(s) -
Wright John B.
Publication year - 1968
Publication title -
journal of heterocyclic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.321
H-Index - 59
eISSN - 1943-5193
pISSN - 0022-152X
DOI - 10.1002/jhet.5570050403
Subject(s) - chemistry , sulfonyl , benzothiadiazine , medicinal chemistry , methyl iodide , derivative (finance) , hydrazine (antidepressant) , organic chemistry , alkyl , financial economics , economics , chromatography
o ‐Benzoylbenzenesulfonyl chlorides (I) were prepared conveniently from aminobenzophenones by diazotization followed by reaction with sulphur dioxide in the presence of Cu + , according to the general method of Meerwein. Reaction of the sulfonyl chlorides with hydrazine led to 4‐phenyl‐2 H ‐1,2,3‐benzothiadiazine‐1,1‐dioxides (II). The latter compounds could be methylated and acetylated readily in the 2‐position. The 2‐methyl derivative (III) could be prepared also by reaction of the sulfonyl chloride (Ia) with methylhydrazine. Catalytic hydrogenation of 6‐chloro‐4‐phenyl‐2 H ‐1,2,3‐benzothiadiazine‐1,1‐dioxide (IIa) gave the 3,4‐dihydro derivative (V). Reaction of the sulfonyl chlorides (I) with o ‐phenylenediamine followed by cyclodehydration led to 11 H ‐11,11a‐dihydrobenzimidazo[1,2‐ b ] [1,2]benzisothiazole‐5,5‐dioxides (VII). One of the latter compounds (VIIa) in sodium hydroxide solution in the presence of methyl iodide or benzyl chloride was transformed into 6‐methyl‐ and 6‐benzyl‐5 H ‐dibenzo[ c,g ] [1,2,6]thiadiazocine‐5,5‐dioxides (VIII), respectively. 5 H ‐Dibenzo[ c,g ] [1,2,6] thiadiazocine‐6,6‐dioxides (XIV) were prepared also by cyclodehydration of 2‐amino‐2′‐benzoylbenzenesulfonanilides (XIII).