Synthesis 2018; 50(13): 2473-2489
DOI: 10.1055/s-0036-1589534
short review
© Georg Thieme Verlag Stuttgart · New York

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

Amanda F. da Silva
Institute of Chemistry, State University of Campinas, Rua Monteiro Lobato 270, 13083-970, Campinas, SP, Brazil   Email: [email protected]
,
Alessandra A. G. Fernandes
Institute of Chemistry, State University of Campinas, Rua Monteiro Lobato 270, 13083-970, Campinas, SP, Brazil   Email: [email protected]
,
Samuel Thurow
Institute of Chemistry, State University of Campinas, Rua Monteiro Lobato 270, 13083-970, Campinas, SP, Brazil   Email: [email protected]
,
Mateus L. Stivanin
Institute of Chemistry, State University of Campinas, Rua Monteiro Lobato 270, 13083-970, Campinas, SP, Brazil   Email: [email protected]
,
Institute of Chemistry, State University of Campinas, Rua Monteiro Lobato 270, 13083-970, Campinas, SP, Brazil   Email: [email protected]
› Author Affiliations
The authors thank FAPESP (2017/24017-0) and CNPq (458416/2014-2) for financial support of our research program. CAPES is acknowledged for Ph.D. fellowships to A.F.S. and A.A.G.F. and a post-doctoral fellowship to S.T. Faepex-Unicamp (127/16) is acknowledged for a M.Sc. fellowship to M.L.S.
Further Information

Publication History

Received: 21 February 2018

Accepted after revision: 03 April 2018

Publication Date:
17 May 2018 (online)


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

 
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