Base-promoted [3 + 3] cyclization of cyclopropenones and cyclopropenethiones with amides for the synthesis of 6H-1,3-oxazin-6-ones and 6H-1,3-thiazin-6-ones

Ben Niu; Bo Jiang; Liu-Zhu Yu; Min Shi

doi:10.1039/C8QO00091C

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Base-promoted [3 + 3] cyclization of cyclopropenones and cyclopropenethiones with amides for the synthesis of 6H-1,3-oxazin-6-ones and 6H-1,3-thiazin-6-ones†

Ben Niu,^a Bo Jiang,^b Liu-Zhu Yu^a and Min Shi

*^abc

Author affiliations

* Corresponding authors

^a Key Laboratory for Advanced Materials and Institute of Fine Chemicals, School of Chemistry & Molecular Engineering, East China University of Science and Technology, Meilong Road No. 130, Shanghai, China

^b State Key Laboratory of Organometallic Chemistry, Center for Excellence in Molecular Synthesis, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 345 Lingling Road, Shanghai 200032, China
E-mail: mshi@mail.sioc.ac.cn

^c State Key Laboratory and Institute of Elemento-organic Chemistry, Nankai University, Tianjin 300071, P. R. China

Abstract

A facile synthetic method to access 6H-1,3-oxazin-6-ones and 6H-1,3-thiazin-6-ones has been disclosed via a base-promoted [3 + 3] cyclization reaction of cyclopropenones and cyclopropenethiones with amides. These reactions exhibited excellent yields and good functional group tolerance under metal free and mild conditions.

This article is part of the themed collections: Celebrating 70 Years of Shanghai Institute of Organic Chemistry and Organic Chemistry Frontiers HOT articles for 2018

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DOI: https://doi.org/10.1039/C8QO00091C
Article type: Research Article
Submitted: 26 Jan 2018
Accepted: 26 Feb 2018
First published: 28 Feb 2018

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Org. Chem. Front., 2018,5, 1267-1271

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Base-promoted [3 + 3] cyclization of cyclopropenones and cyclopropenethiones with amides for the synthesis of 6H-1,3-oxazin-6-ones and 6H-1,3-thiazin-6-ones

B. Niu, B. Jiang, L. Yu and M. Shi, Org. Chem. Front., 2018, 5, 1267 DOI: 10.1039/C8QO00091C

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Organic Chemistry Frontiers

Base-promoted [3 + 3] cyclization of cyclopropenones and cyclopropenethiones with amides for the synthesis of 6H-1,3-oxazin-6-ones and 6H-1,3-thiazin-6-ones†

Abstract

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Base-promoted [3 + 3] cyclization of cyclopropenones and cyclopropenethiones with amides for the synthesis of 6H-1,3-oxazin-6-ones and 6H-1,3-thiazin-6-ones

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