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Synthesis of Cyanide‐Functionalized Imidazo[1,5‐a]quinolines via Copper‐Mediated Aerobic Three‐Component Cyclizations
Author(s) -
Feng ChengTao,
Wei HongJuan,
Li Jing,
Peng Ya,
Xu Kun
Publication year - 2018
Publication title -
advanced synthesis and catalysis
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.541
H-Index - 155
eISSN - 1615-4169
pISSN - 1615-4150
DOI - 10.1002/adsc.201801060
Subject(s) - chemistry , trimethylsilyl cyanide , yield (engineering) , cyanide , copper , combinatorial chemistry , component (thermodynamics) , oxygen , functional group , organic chemistry , catalysis , materials science , physics , metallurgy , thermodynamics , polymer
A three‐component cyclization of 2‐methylquinolines, trimethylsilyl cyanide, and alkylamines or α‐amino acids mediated by CuSO 4 was developed. By employing oxygen as the clean oxidant, cyanated imidazo[1,5‐a]quinolines were constructed with high efficiency for the first time. The loading of CuSO 4 could be lowered to 20 mol% with a slightly diminished yield. The synthetic utility of this method is further highlighted by the gram‐scale synthesis and tolerance of sensitive functional group.