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

Pedro F. Soeiro; João L. Serrano; José A. Paixão; Renato E. F. Boto; Samuel Silvestre; Paulo Almeida

doi:10.1055/s-0039-1690865

Synthesis, Table of Contents

Synthesis 2020; 52(14): 2065-2072
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

Pedro F. Soeiro

^aCICS-UBI - Health Sciences Research Center, University of Beira Interior, Av. Infante D. Henrique, 6201-506 Covilhã, Portugal

^bDepartment of Chemistry, University of Beira Interior, Rua Marquês d’Ávila e Bolama, 6201-001 Covilhã, Portugal Email: paulo.almeida@ubi.pt

,

João L. Serrano

^aCICS-UBI - Health Sciences Research Center, University of Beira Interior, Av. Infante D. Henrique, 6201-506 Covilhã, Portugal

^bDepartment of Chemistry, University of Beira Interior, Rua Marquês d’Ávila e Bolama, 6201-001 Covilhã, Portugal Email: paulo.almeida@ubi.pt

,

José A. Paixão

^cCFisUC, Department of Physics, University of Coimbra, Rua Larga, 3004-516 Coimbra, Portugal

,

Renato E. F. Boto

^aCICS-UBI - Health Sciences Research Center, University of Beira Interior, Av. Infante D. Henrique, 6201-506 Covilhã, Portugal

^bDepartment of Chemistry, University of Beira Interior, Rua Marquês d’Ávila e Bolama, 6201-001 Covilhã, Portugal Email: paulo.almeida@ubi.pt

,

Samuel Silvestre

^aCICS-UBI - Health Sciences Research Center, University of Beira Interior, Av. Infante D. Henrique, 6201-506 Covilhã, Portugal

^dCNC – Center for Neuroscience and Cell Biology, University of Coimbra, Rua Larga, 3004-517 Coimbra, Portugal

,

Paulo Almeida ∗

^aCICS-UBI - Health Sciences Research Center, University of Beira Interior, Av. Infante D. Henrique, 6201-506 Covilhã, Portugal

^bDepartment of Chemistry, University of Beira Interior, Rua Marquês d’Ávila e Bolama, 6201-001 Covilhã, Portugal Email: paulo.almeida@ubi.pt

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Abstract

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§ 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

Full Text

References

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