Issue 16, 2019

A concise construction of 4-alkynylquinazolines via [4 + 2] annulation of 4-alkynylbenzoxazinanones with acylhydroxamates under transition-metal-free conditions

Abstract

A concise and highly efficient method for the construction of valuable 4-alkynylquinazolines under transition-metal-free conditions was developed via [4 + 2] annulation of 4-alkynylbenzoxazinanones with acylhydroxamates in good to excellent yields. The reaction featured the use of low-cost bases NaOAc or NaOMe, simple operation and high chemoselectivity. The broad substrate scope and the typical maintenance of high efficiency on a gram scale made this protocol a potentially practical method to synthesize 4-alkynylquinazolines.

Graphical abstract: A concise construction of 4-alkynylquinazolines via [4 + 2] annulation of 4-alkynylbenzoxazinanones with acylhydroxamates under transition-metal-free conditions

Supplementary files

Article information

Article type
Research Article
Submitted
20 May 2019
Accepted
26 Jun 2019
First published
28 Jun 2019

Org. Chem. Front., 2019,6, 2892-2896

A concise construction of 4-alkynylquinazolines via [4 + 2] annulation of 4-alkynylbenzoxazinanones with acylhydroxamates under transition-metal-free conditions

W. Yuan, S. Sun, L. Zhang, L. Wen and M. Li, Org. Chem. Front., 2019, 6, 2892 DOI: 10.1039/C9QO00668K

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