European Journal of Organic Chemistry 2018-02-15

Synthesis of 2‐acetylbenzonitriles and reactivity in tandem reactions with carbon‐ and hetero‐nucleophiles: easy access to 3,3‐disubstituted isoindolinones.

Antonia Di Mola; Miriam Di Martino; Vito Capaccio; Giovanni Pierri; Laura Palombi; Consiglia Tedesco; Antonio Massa

Index: 10.1002/ejoc.201800240

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Abstract

The synthesis of 2‐acetylbenzonitriles has been conveniently achieved by oxidation of the respective 2‐ethylbenzonitriles, combining in one‐pot procedures radical bromination and hydrolysis reaction. The obtained ketones, reacted under very mild conditions with carbon‐ and hetero‐nucleophiles, led to a wide range of 3,3‐disubstituted isoindolinones in yields of 80 to 99% via 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 catalytic amount of KOH allowed a convenient access to an unprecedented variety of novel 3‐hydroxy‐3‐methyl isoindolinones.

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