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Catalyst‐Free Three‐Component Tandem CDC Cyclization: Convenient Access to Isoindolinones from Aromatic Acid, Amides, and DMSO by a Pummerer‐Type Rearrangement
Author(s) -
Wang PengMin,
Pu Fan,
Liu KeYan,
Li ChaoJun,
Liu ZhongWen,
Shi XianYing,
Fan Juan,
Yang MingYu,
Wei JunFa
Publication year - 2016
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201600865
Subject(s) - tandem , chemistry , component (thermodynamics) , pummerer rearrangement , catalysis , combinatorial chemistry , organic chemistry , materials science , physics , acetic anhydride , thermodynamics , composite material
A catalyst‐free multicomponent CDC reaction is rarely reported, especially for the intermolecular tandem CDC cyclization, which represents an important strategy for constructing cyclic compounds. Herein, a three‐component tandem CDC cyclization by a Pummerer‐type rearrangement to afford biologically relevant isoindolinones from aromatic acids, amides, and DMSO, is described. This intermolecular tandem reaction undergoes a C(sp 2 )−H/C(sp 3 )−H cross‐dehydrogenative coupling, C−N bond formation, and intramolecular amidation. A notable feature of this novel protocol is avoiding a catalyst and additive (apart from oxidant).