Abstract
AbstractThe cycloisomerization of readily available 2‐alkynylbenzamides has been conveniently carried out with CuCl2 as catalyst under basic conditions in 1‐ethyl‐3‐methylimidazolium ethyl sulfate (EmimEtSO4) as an unconventional solvent. The process leads to (Z)‐3‐alkylideneisoindolin‐1‐ones in a chemo‐, regio‐, and stereoselective manner. The catalyst/solvent/base system could be recycled several times without appreciable loss of activity. The structures of representative products, that are, (Z)‐3‐benzylidene‐2‐phenylisoindolin‐1‐one and (Z)‐3‐pentylidene‐2‐phenylisoindolin‐1‐one, have been confirmed by X‐ray diffraction analysis, and DFT (density functional theory) calculations have been carried out to clarify the roles exerted by the base and CuCl2 in favoring the reaction course leading to (Z)‐3‐alkylideneisoindolinones.
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