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Synthesis 2020; 52(14): 2065-2072
DOI: 10.1055/s-0039-1690865
DOI: 10.1055/s-0039-1690865
paper
The Synthesis of 2-Spiroindolin-3-one-(thio)barbiturates from 2,1-Benzisoxazoles: A Rearrangement Promoted by Thermal Conditions
This work is supported by funds from the Health Sciences Research Center (CICS-UBI) (UID/Multi/00709/2019) and from CFisUC, Department of Physics (UID/FIS/4564/2019) through National Funds by Fundação para a Ciência e Tecnologia (FCT). This work is also supported by FEDER funds through the POCI–COMPETE 2020–Operational Programme Competitiveness and Internationalization in Axis I–Strengthening research, technological development and innovation [Programa Operacional Competitividade e Internacionalização (COMPETE 2020), project No. 007491)]. J. L. Serrano acknowledges a doctoral fellowship grant from the FCT (SFRH/BD/148028/2019) and a fellowship from Santander-Totta/UBI (BID/ICI-UID FC/Santander Universidades-UBI/2017).Further Information
Publication History
Received: 23 January 2020
Accepted after revision: 06 March 2020
Publication Date:
24 March 2020 (online)
§ 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 irradiationSupporting Information
- Supporting information for this article is available online at https://doi.org/10.1055/s-0039-1690865.
- Supporting Information
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For medicinal applications of spiroindolinones, see:
For biological activities of barbiturates, see:
For examples of C5 spiro-(thio)barbiturates bound to 3- to 7-membered rings, see: