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Copper‐Mediated Tandem C( sp 2 )–H Sulfenylation and Annulation of Arenes with 2‐Mercaptoimidazoles: Regio‐ and Site‐selective Access to Polycyclic Fused Imidazo[2,1‐ b ][1,3]thiazinones
Author(s) -
Liu Jidan,
Xue Zixi,
Zeng Zhizhao,
Chen Yixin,
Chen Guoshu
Publication year - 2016
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.201600775
Subject(s) - chemistry , annulation , intramolecular force , amide , tandem , nucleophilic aromatic substitution , stereochemistry , denticity , oxazoline , medicinal chemistry , ring (chemistry) , nucleophilic addition , combinatorial chemistry , nucleophilic substitution , organic chemistry , metal , catalysis , materials science , composite material
An efficient copper‐mediated tandem C( sp 2 )–H sulfenylation and annulation of arenes with 2‐mercaptoimidazoles to provide polycyclic fused imidazo[2,1‐ b ][1,3]thiazinones has been developed. This tandem reaction is likely initiated by C( sp 2 )–H thiolation of benzamide with 2‐mercaptoimidazole followed by intramolecular nucleophilic substitution of the amide carbonyl group. A notable feature of this reaction is that it can afford rather complex products in a single synthesis step from easily accessible starting materials using amide‐oxazoline as a removable bidentate directing group. A variety of benzamides and 2‐mercaptoimidazoles bearing different substituents are compatible with this transformation.