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Metal‐Free Oxidative [5+1] Cyclization of 1,5‐Enynes for the Synthesis of Pyrazine 1‐Oxide
Author(s) -
Xia XiaoFeng,
Zhao Mingming,
He Wei,
Zou Lianghua,
San Xinxin,
Wang Dawei
Publication year - 2020
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.202000756
Subject(s) - chemistry , pyrazine , intramolecular force , cycloaddition , combinatorial chemistry , oxide , nitrosylation , reaction conditions , photochemistry , organic chemistry , nitric oxide , catalysis
A chemo‐selective nitrosylation of 1,5‐enynes via a sequence of NO radical incorporation and intramolecular radical cyclization was reported. The formation of two C−N bonds and one C−O bond make this [5+1] cycloaddition reaction an efficient approach to synthesize pyrazine 1‐oxides in moderate to good yields. Metal‐free, short reaction time and mild conditions render this strategy more practical, eco‐friendly and convenient. Synthetic utility of this protocol is highlighted by scaffolds diversification.