Rhodium-catalyzed transannulation of N-sulfonyl-1,2,3-triazoles and epoxides: regioselective synthesis of substituted 3,4-dihydro-2H-1,4-oxazines

Xueji Ma; Shanfei Pan; Hangxiang Wang; Wanzhi Chen

doi:10.1021/ol5021042

Rhodium-catalyzed transannulation of N-sulfonyl-1,2,3-triazoles and epoxides: regioselective synthesis of substituted 3,4-dihydro-2H-1,4-oxazines

Org Lett. 2014 Sep 5;16(17):4554-7. doi: 10.1021/ol5021042. Epub 2014 Aug 21.

Authors

Xueji Ma¹, Shanfei Pan, Hangxiang Wang, Wanzhi Chen

Affiliation

¹ Department of Chemistry, Zhejiang University , Hangzhou 310028, People's Republic of China.

PMID: 25144463
DOI: 10.1021/ol5021042

Abstract

Rhodium-catalyzed transannulation of 1,2,3-triazoles and ring-opening reactions of epoxides is described. A number of 3,4-dihydro-2H-1,4-oxazines are obtained in moderate yields probably involving generation of α-imino rhodium(II) carbene species.

Publication types

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

MeSH terms

Catalysis
Combinatorial Chemistry Techniques
Methane / analogs & derivatives
Methane / chemical synthesis
Molecular Structure
Oxazines / chemical synthesis*
Oxazines / chemistry
Rhodium / chemistry*
Triazoles / chemistry*

Substances

Oxazines
Triazoles
carbene
Rhodium
Methane