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

You do not have JavaScript enabled. Please enable JavaScript to access the full features of the site or access our non-JavaScript page.

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

Download options Please wait...

Supplementary files

Article information

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

Download Citation

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

Permissions

Request permissions

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

To request permission to reproduce material from this article, please go to the Copyright Clearance Center request page.

If you are an author contributing to an RSC publication, you do not need to request permission provided correct acknowledgement is given.

If you are the author of this article, you do not need to request permission to reproduce figures and diagrams provided correct acknowledgement is given. If you want to reproduce the whole article in a third-party publication (excluding your thesis/dissertation for which permission is not required) please go to the Copyright Clearance Center request page.

Social activity

Fetching data from CrossRef.
This may take some time to load.

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

Supplementary files

Article information

Download Citation

Permissions

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

Social activity

Search articles by author

Spotlight

Advertisements