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γ ‐Functionalization of α,β ‐Unsaturated Nitriles under Mild Conditions: Versatile Synthesis of 4‐Aryl‐2‐Bromopyridines
Author(s) -
Sim Jaeuk,
Viji Mayavan,
Rhee Jeongtae,
Jo Hyeju,
Cho Suk Joon,
Park Yunjeong,
Seo SeungYong,
Jung KwanYoung,
Lee Heesoon,
Jung JaeKyung
Publication year - 2019
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.201901002
Subject(s) - chemistry , nitrile , surface modification , intramolecular force , aryl , enamine , combinatorial chemistry , conjugated system , organic chemistry , catalysis , polymer , alkyl
This report describes the synthesis of 4‐aryl‐2‐halopyridines via γ ‐functionalization of α,β ‐unsaturated nitriles, which were obtained by the HWE reaction with the corresponding ketones. The key features of our methods involve a conjugated γ‐ enamine formation of α,β ‐unsaturated nitrile (enamino nitrile), followed by consecutive intramolecular cyclization, resulting in heteroaromatic compounds like 2‐halopyridines, α ‐pyrone, etc.