153529-60-3

Upstream product

• 153529-51-2 [7-(2-Hydroxy-2-phenyl-ethyl)-benzotriazol-1-yl]-carbamic acid tert-butyl ester 
• 21978-58-5 7-methyl-benzotriazol-1-ylamine 
• 153529-47-6 1-(tert-butyloxycarbonylamino)-7-methylbenzotriazole 
• 153529-46-5 1-[Bis(tert-butoxycarbonyl)amino]-7-methylbenzotriazole 

Relevant academic research and scientific papers

A new approach to dihydrobenzofurans and dihydrobenzopyrans (chromans) based on the intramolecular trapping by alcohols of benzynes generated from 7-substituted-1-aminobenzotriazoles

1-Aminobenzotriazoles 9 having 7-hydroxyalkyl substituents are efficiently convened into the corresponding benzynes 4 when treated with N- iodosuccinimide which then undergo highly efficient intramolecular trapping by the pendant hydroxyl groups leading to dihydrobenzofurans 24-26 and dihydrobenzopyrans (chromans) 27, with incorporation of a synthetically useful iodine atom adjacent to the new ether bond, which allows subsequent and high-yielding homologations using Stille, Sonogashira and Heck couplings. (C) 2000 Elsevier Science Ltd.

A route to ortho-substituted benzyne precursors by deprotonation of 7-methyl-1-aminobenzotriazole derivatives

Double deprotonation of N-Boc-7-methyl-1-aminobenzotriazole 6 using (n)BuLi-TMEDA-THF [-78°C -> 0°C) results in an essentially quantitative conversion to the dianionic intermediate 7. Trapping at the carbon-centred anion occurs selectively under suitable conditions with alkylating agents, aldehydes and ketones to give good the excellent yields of the 7-substituted-1-aminobenzotriazoles 8-15, precursors of ortho-substituted benzynes.