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Treatment of 1-chloromethylbenzotriazole (4) with salicylonitrile (5a), thiosalicylonitrile (5b), ethyl N-(2-cyanophenyl)carbamate (5c), and N-(2-cyanophenyl)methane-sulfonamide (5d) provided the corresponding intermediates 3. Cyclization of compounds 3a-3c with LDA gave 2- (1H-benzo(d)(1,2,3)triazol-1-yl)benzofuran-3-amine (2a), 2-(1H-benzo(d)(1,2,3)triazol-1- yl)benzo(b)thiophen-3-amine (2b), and ethyl 3-amino-2-(1H-benzo(d)(1,2,3)triazol-1-yl)-1H- indole-1-carboxylate (2c), respectively. Attempts to accomplish elimination of the benzotriazole nitrogen under both thermal and photolytic conditions failed.

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Modification of the Gewald reaction for the synthesis of 3-amino-2-(1H-1,2,3-benzotriazol-1-yl) substituted benzofurans, benzothiophenes and 1H-indoles