The Synthesis of 2-Spiroindolin-3-one-(thio)barbiturates from 2,1-Benzisoxazoles: A Rearrangement Promoted by Thermal Conditions

§ These authors contributed equally to this manuscript.

Abstract

A new thermal process to prepare spiroindolin-3-ones from 3-substituted 2,1-benzisoxazoles in good yields (70–85%) is described. The highest yields were observed when microwave irradiation was used. The method does not require the use of any additive or catalyst. A possible reaction mechanism involving a nitrene key intermediate is proposed.

Key words

2-spiroindolin-3-one - (thio)barbiturate - 2,1-benzisoxazole - thermal rearrangement - microwave irradiation

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