Issue 6, 2016
From the journal:

Organic Chemistry Frontiers

Straightforward regioselective construction of 3,4-dihydro-2H-1,4-thiazine by rhodium catalysed [3 + 3] cycloaddition of thiirane with 1-sulfonyl-1,2,3-triazole: a pronounced acid additive effect†

Xiao-Long Lu,a   Ya-Ting Liu,a   Qing-Xia Wang,a   Mei-Hua Shen*a  and  Hua-Dong Xu*a  

* Corresponding authors

a School of Pharmaceutical Engineering and Life Science, Changzhou University, Changzhou 213164, China
E-mail: shemmh@cczu.edu.cn, huadongxu@gmail.com

Abstract

A rhodium catalyzed regioselective coupling of thiirane with 1-sulfonyl-1,2,3-triazole has been realized to give a formal [3 + 3] cycloaddition product 3,4-dihydro-2H-1,4-thiazine via the 1,3-insertion model of azavinyl carbene. An acetic acid additive is used to improve the reaction in terms of both yield and rate.

Graphical abstract: Straightforward regioselective construction of 3,4-dihydro-2H-1,4-thiazine by rhodium catalysed [3 + 3] cycloaddition of thiirane with 1-sulfonyl-1,2,3-triazole: a pronounced acid additive effect

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Article information

DOI
https://doi.org/10.1039/C6QO00084C
Article type
Research Article
Submitted
01 Mar 2016
Accepted
30 Mar 2016
First published
31 Mar 2016

Org. Chem. Front., 2016,3, 725-729

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Straightforward regioselective construction of 3,4-dihydro-2H-1,4-thiazine by rhodium catalysed [3 + 3] cycloaddition of thiirane with 1-sulfonyl-1,2,3-triazole: a pronounced acid additive effect

X. Lu, Y. Liu, Q. Wang, M. Shen and H. Xu, Org. Chem. Front., 2016, 3, 725 DOI: 10.1039/C6QO00084C

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