Copper-catalyzed oxidative ring closure and carboarylation of 2-ethynylanilides

Ádám Sinai; Ádám Mészáros; Tamás Gáti; Veronika Kudar; Anna Palló; Zoltán Novák

doi:10.1021/ol402600r

Copper-catalyzed oxidative ring closure and carboarylation of 2-ethynylanilides

Org Lett. 2013 Nov 15;15(22):5654-7. doi: 10.1021/ol402600r. Epub 2013 Nov 4.

Authors

Ádám Sinai¹, Ádám Mészáros, Tamás Gáti, Veronika Kudar, Anna Palló, Zoltán Novák

Affiliation

¹ MTA-ELTE "Lendület" Catalysis and Organic Synthesis Research Group, Institute of Chemistry, Eötvös University , Pázmány Péter stny. 1/a, H-1117 Budapest, Hungary , Servier Research Institute of Medicinal Chemistry , Záhony utca 7, H-1031 Budapest, Hungary , and Research Centre for Natural Sciences, Hungarian Academy of Sciences , Pusztaszeri út 59-67, H-1025 Budapest, Hungary.

PMID: 24188109
DOI: 10.1021/ol402600r

Abstract

A new copper-catalyzed oxidative ring closure of ethynyl anilides with diaryliodonium salts was developed for the highly modular construction of benzoxazines bearing a fully substituted exo double bond. The oxidative transformation includes an unusual 6-exo-dig cyclization step with the formation of C-O and C-C bonds.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Anilides / chemistry*
Benzoxazines / chemical synthesis*
Benzoxazines / chemistry
Catalysis
Copper / chemistry*
Cyclization
Molecular Structure
Onium Compounds / chemistry*
Oxidation-Reduction

Substances

Anilides
Benzoxazines
Onium Compounds
Copper