Synthetic transformations of 1-cyanomethylbenzotriazole

✍ Scribed by Alan R. Katritzky; Jie Chen; Zhijun Yang

• Publisher: John Wiley and Sons
• Year: 1995
• Tongue: English
• Weight: 476 KB
• Volume: 6
• Category: Article
• ISSN: 1042-7163
• DOI: 10.1002/hc.520060115

✦ Synopsis

Lithiation of 1 -cyanomethylbenzotriazole (4) with LDA and subsequent reactions with alkyl halides or car-bony1 compounds afforded the cowesponding 1 -(a- cyanoalky1)-and 1-(a-cyanoalkeny1)-benzotriazoles.

Bromination of 4 with NBS formed 1 -(brornocyanomethyl) benzotriazole.

1 -Cyanoalkylbenzotriazoles condensed with hydrazine hydrate to give 4-amino-3,5-bis(benzotriazol-l-yl)triazoles which underwent deamination with sodium nitrite to yield 3,5bis(benzotriazo1-1 -yl)triazoles.