Oxindoles display a diverse pattern of reactivity upon reaction with different classes of amino alcohols via the borrowing hydrogen process. Whereas the reaction with N-acetyl amino alcohols leads to C3 alkylation, the reaction with N-alkyl amino alcohols results in the formation of synthetically useful α-aryl-lactams via a remarkably facile oxindole ring-opening reaction. Reactions occurred with quantitative conversion and selectivity under relatively mild reaction conditions.

Divergent reactions of oxindoles with amino alcohols via the borrowing hydrogen process: oxindole ring opening vs. C3 alkylation

Di Gregorio, Giovanni;Mari, Michele;Bartolucci, Silvia;Bartoccini, Francesca;Piersanti, Giovanni
2018

Abstract

Oxindoles display a diverse pattern of reactivity upon reaction with different classes of amino alcohols via the borrowing hydrogen process. Whereas the reaction with N-acetyl amino alcohols leads to C3 alkylation, the reaction with N-alkyl amino alcohols results in the formation of synthetically useful α-aryl-lactams via a remarkably facile oxindole ring-opening reaction. Reactions occurred with quantitative conversion and selectivity under relatively mild reaction conditions.
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Utilizza questo identificativo per citare o creare un link a questo documento: https://hdl.handle.net/11576/2660417
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