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Synthesis of [1,2,3]‐Triazolo[5,1‐ a ]‐isoquinolines through TBAF‐Promoted Cascade Reactions
Author(s) -
Duan Shengguo,
Chen Yidian,
Meng Hui,
Shan Lihong,
Xu ZeFeng,
Li ChuanYing
Publication year - 2021
Publication title -
asian journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.846
H-Index - 44
eISSN - 2193-5815
pISSN - 2193-5807
DOI - 10.1002/ajoc.202000618
Subject(s) - chemistry , reagent , yield (engineering) , tetrabutylammonium fluoride , halogen , fluoride , cascade , organic chemistry , deuterium , combinatorial chemistry , cascade reaction , catalysis , inorganic chemistry , materials science , alkyl , physics , quantum mechanics , metallurgy , chromatography
A tetrabutylammonium fluoride (TBAF)‐promoted detosylation cyclization cascade was developed for the synthesis of [1,2,3]‐triazolo[5,1‐ a ]‐isoquinolines. Most of the products were obtained in excellent yields under mild conditions. Valuable halogen‐substituted [1,2,3]‐triazolo[5,1‐ a ]‐isoquinolines could also be synthesized with a slight modification of the reaction conditions. Functionalized isoquinolines were obtained smoothly by denitrogenative reactions. The control experiments showed that this transformation was facilitated by TBAF and the water contained in the commercially obtained reagent. Deuterium labeling products could also be obtained easily in high yield.