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Reactions with 1,8‐naphthosultam. Synthesis of [1,2]benzisothiazolo[2,3,4‐ cde ]benzotriazole 4,4‐dioxide. A new ring system
Author(s) -
Hammouda Hamdy A.,
ElReedy Ahmed M.,
Sharaf Mohie A. F.,
AbdelFattah A. M.
Publication year - 1984
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.5570210213
Subject(s) - chemistry , benzotriazole , ring (chemistry) , nitrous acid , medicinal chemistry , nitro , stereochemistry , organic chemistry , alkyl
1,8‐Naphthosultam (I) coupled with arenediazonium salts to give the 4‐arylazo‐ VII, and the 2,4‐bisarylazo‐1,8‐naphthosultams, VIa‐c. On the other hand, coupling of the 4‐substituted 1,8‐naphthosultams afforded the 2‐phenylazo derivatives, IIa,b. Reduction of IIa,b gave the 2‐amino compounds IVa,b, which reacted with nitrous acid to give the [1,2]benzisothiazolo[2,3,4‐ cde ]benzotriazoles, Va,b, establishing thus a new ring system. The nitro analogue Vc was also synthesized.