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Abstract
Isoindolinone is a class
of versatile N-heterocycles embedded in
many bioactive molecules and natural products. The invention of new methods to synthesize
these heterocyclic compounds with easily accessible chemicals is always attractive.
Herein, a conceptually novel approach to access this bicyclic system via isonitrile
insertion enabled 1,4-pallaidum shift is described. Compared with conventional
isonitrile participated C-H bond activation, both carbon and nitrogen atoms in
isonitrile moiety are engaged in new bond formation. Notably, two different
isoindolinones can be obtained selectively by switching the bases employed. Mechanistic
studies including DFT calculations have shed lights on the reaction mechanism
and explained the selectivity led to different products. Moreover, the power of
current benzolactamization is further demonstrated by providing concise routes
to key intermediates of indoprofen, indobufen, aristolactams, lennoxamine and
falipamil.
Supplementary materials
Title
ChemRxiv SI
Description
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