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Synthesis and Reactivity of the 3‐Substituted Isoindolinone Framework to Assemble Highly Functionalized Related Structures
Author(s) -
Petronzi Carmen,
Collarile Selene,
Croce Gianluca,
Filosa Rosanna,
De Caprariis Paolo,
Peduto Antonella,
Palombi Laura,
Intintoli Valentina,
Di Mola Antonia,
Massa Antonio
Publication year - 2012
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201200678
Subject(s) - chemistry , hemiaminal , tandem , aldol reaction , reactivity (psychology) , combinatorial chemistry , methylene , potassium carbonate , catalysis , organic chemistry , medicine , materials science , alternative medicine , pathology , composite material
An efficient potassium carbonate‐catalyzed synthesis of 3‐substituted isoindolinones through tandem aldol/cyclization reactions of active methylene compounds with 2‐cyanobenzaldehyde is described. The utility of the obtained isoindolinones has been demonstrated through an exploration of the chemical space by employing a series of interesting methodologies that led to diverse, highly functionalized compounds. Among them, a surprisingly straightforward potassiumcarbonate‐catalyzed double tandem reaction led to tricyclic hemiaminal derivatives.