Hypervalent Iodine(III)‐Mediated Regioselective Cyanation of Quinoline N‐Oxides with Trimethylsilyl Cyanide

A regioselective cyanation of quinoline N‐oxides with trimethylsilyl cyanide was developed by using (Diacetoxyiodo) benzene (PIDA) as mediated hypervalent iodine(III) reagent under metal‐free and base‐free reaction conditions to obtain 2‐cyanoquinolines. The efficient PIDA reagent could play the rol...

Full description

Saved in:
Bibliographic Details
Published in:Advanced synthesis & catalysis 2019-02, Vol.361 (3), p.520-525
Main Authors: Xu, Feng, Li, Yuqin, Huang, Xin, Fang, Xinjie, Li, Zhuofei, Jiang, Hongshuo, Qiao, Jingyi, Chu, Wenyi, Sun, Zhizhong
Format: Article
Language:English
Subjects:
Benzene
Cyanation
Cyanides
Iodine
Metal-free
PIDA
Quinoline
Quinoline N-oxides
Reagents
Regioselectivity
Substrates
Trimethylsilyl cyanide
Tuberculosis
Citations: Items that this one cites
Items that cite this one
Online Access:Get full text
Tags: Add Tag
No Tags, Be the first to tag this record!
Description
Summary:A regioselective cyanation of quinoline N‐oxides with trimethylsilyl cyanide was developed by using (Diacetoxyiodo) benzene (PIDA) as mediated hypervalent iodine(III) reagent under metal‐free and base‐free reaction conditions to obtain 2‐cyanoquinolines. The efficient PIDA reagent could play the role of an activator of the substrates and an accelerator of N−O bond cleavage. The reaction system featured a wide range of substrate suitability and high yields. The procedure was enlarged gram‐scale to synthesize the tuberculosis (TB) inhibitor. Finally, according to some experimental results, a plausible mechanism for the cyanation reaction is proposed.
ISSN:1615-4150
1615-4169
DOI:10.1002/adsc.201801185