Synthesis of Cyanide‐Functionalized Imidazo[1,5‐a]quinolines via Copper‐Mediated Aerobic Three‐Component Cyclizations

A three‐component cyclization of 2‐methylquinolines, trimethylsilyl cyanide, and alkylamines or α‐amino acids mediated by CuSO4 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 CuSO4 co...

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Published in:Advanced synthesis & catalysis 2018-12, Vol.360 (24), p.4726-4730
Main Authors: Feng, Cheng‐Tao, Wei, Hong‐Juan, Li, Jing, Peng, Ya, Xu, Kun
Format: Article
Language:English
Subjects:
Alkylamines
Amino acids
Copper catalysis
Copper sulfate
Cyanated heterocycle
Cyanides
Functional groups
Imidazo[1,5-a]quinoline
Organic compounds
Synthesis
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cited_by cdi_FETCH-LOGICAL-c3540-6aec08729edf67a03884939c15855cd0defddc65b3b7444f08811e248853a8c93
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description A three‐component cyclization of 2‐methylquinolines, trimethylsilyl cyanide, and alkylamines or α‐amino acids mediated by CuSO4 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 CuSO4 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.
doi_str_mv 10.1002/adsc.201801060
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subjects Alkylamines
Amino acids
Copper catalysis
Copper sulfate
Cyanated heterocycle
Cyanides
Functional groups
Imidazo[1,5-a]quinoline
Organic compounds
Synthesis
title Synthesis of Cyanide‐Functionalized Imidazo[1,5‐a]quinolines via Copper‐Mediated Aerobic Three‐Component Cyclizations
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