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Synthesis of 2‐Acetylbenzonitriles and Their Reactivity in Tandem Reactions with Carbon and Hetero Nucleophiles: Easy Access to 3,3‐Disubstituted Isoindolinones
Author(s) -
Di Mola Antonia,
Di Martino Miriam,
Capaccio Vito,
Pierri Giovanni,
Palombi Laura,
Tedesco Consiglia,
Massa Antonio
Publication year - 2018
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.201800240
Subject(s) - nucleophile , chemistry , reactivity (psychology) , tandem , halogenation , catalysis , hydrolysis , carbon fibers , combinatorial chemistry , organic chemistry , composite number , medicine , materials science , alternative medicine , pathology , composite material
2‐Acetylbenzonitriles have been conveniently synthesized by the oxidation of the respective 2‐ethylbenzonitriles, combining in a one‐pot procedure radical bromination and hydrolysis reactions. The obtained ketones reacted under very mild conditions with carbon and hetero nucleophiles to give a wide range of 3,3‐disubstituted isoindolinones in yields of 80–99 % by a tandem process consisting of an addition step and a subsequent Dimroth‐type rearrangement. Among the tested nucleophiles, the addition of water in the presence of a catalytic amount of KOH allowed a convenient access to an unprecedented variety of novel 3‐hydroxy‐3‐methylisoindolinones.