Isoxazol-5-ones as Strategic Building Blocks in Organic Synthesis

Amanda F. da Silva; Alessandra A. G. Fernandes; Samuel Thurow; Mateus L. Stivanin; Igor D. Jurberg

doi:10.1055/s-0036-1589534

Synthesis, Table of Contents

Synthesis 2018; 50(13): 2473-2489
DOI: 10.1055/s-0036-1589534

short review

Isoxazol-5-ones as Strategic Building Blocks in Organic Synthesis

Authors

Amanda F. da Silva

Institute of Chemistry, State University of Campinas, Rua Monteiro Lobato 270, 13083-970, Campinas, SP, Brazil Email: idjurberg@iqm.unicamp.br
Alessandra A. G. Fernandes

Institute of Chemistry, State University of Campinas, Rua Monteiro Lobato 270, 13083-970, Campinas, SP, Brazil Email: idjurberg@iqm.unicamp.br
Samuel Thurow

Institute of Chemistry, State University of Campinas, Rua Monteiro Lobato 270, 13083-970, Campinas, SP, Brazil Email: idjurberg@iqm.unicamp.br
Mateus L. Stivanin

Institute of Chemistry, State University of Campinas, Rua Monteiro Lobato 270, 13083-970, Campinas, SP, Brazil Email: idjurberg@iqm.unicamp.br
Igor D. Jurberg *

Institute of Chemistry, State University of Campinas, Rua Monteiro Lobato 270, 13083-970, Campinas, SP, Brazil Email: idjurberg@iqm.unicamp.br

Abstract

All articles of this category

Abstract

Isoxazol-5-one rings have been identified as relevant motifs in drug candidates, agrochemicals, and materials. Furthermore, this heterocycle has been also applied as a versatile building block for the preparation of a variety of densely functionalized molecules. This short review will present the most representative applications of isoxazol-5-ones in organic synthesis while discussing their properties and reactivity.

1 Introduction

1.1 General Aspects

1.1.1 Tautomerism

1.1.2 Importance: Natural Products Isolation, Biological Activity, and Materials

1.1.3 Preparation Methods

2 Isoxazol-5-ones in Organic Synthesis

2.1 General Reactivity

2.2 Specific Examples

2.2.1 Alkylation Strategies

2.2.2 Alkyne Synthesis

2.2.3 Annulation Reactions

2.2.4 N–O Bond Insertions

2.2.4.1 Preparation of 1,3-Oxazin-6-ones

3 Conclusions

Key words

isoxazol-5-ones - heterocycles - decarboxylation - alkynes - 2H-azirines - pyridines - 1,3-oxazin-6-ones

Full Text

References

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