Rhodium/Silver-Cocatalyzed Transannulation of N-Sulfonyl-1,2,3-triazoles with Vinyl Azides: Divergent Synthesis of Pyrroles and 2 H-Pyrazines

Lin Zhang; Ge Sun; Xihe Bi

doi:10.1002/asia.201601164

Rhodium/Silver-Cocatalyzed Transannulation of N-Sulfonyl-1,2,3-triazoles with Vinyl Azides: Divergent Synthesis of Pyrroles and 2 H-Pyrazines

Chem Asian J. 2016 Nov 7;11(21):3018-3021. doi: 10.1002/asia.201601164. Epub 2016 Oct 12.

Authors

Lin Zhang¹, Ge Sun², Xihe Bi^{1

3}

Affiliations

¹ Jilin Province Key Laboratory of Organic Functional Molecular Design & Synthesis, Department of Chemistry, Northeast Normal University, Renmin Str. 5268#, Changchun, 130024, China.
² College of Pharmacy, Qiqihar Medical University, 333 Bukui Street, 161006, Qiqihar, China.
³ State Key Laboratory of Elemento-Organic Chemistry, Nankai University, Tianjin, 300071, China.

PMID: 27643511
DOI: 10.1002/asia.201601164

Abstract

The first cyclization reaction between vinyl azides and N-sulfonyl-1,2,3-triazoles is reported. A Rh/Ag binary metal catalyst system proved to be necessary for the successful cyclization. By varying the structure of vinyl azides, such reaction allows the divergent synthesis of pyrroles and 2H-pyrazines. The cyclization reactions feature a broad substrate scope, good functional group tolerance, high reaction efficiency, and good to high product yields.

Keywords: pyrazines; pyrroles; rhodium; silver; sulfonyl-1,2,3-triazoles; vinyl azides.

MeSH terms

Azides / chemistry*
Catalysis
Cyclization
Pyrazines / chemical synthesis
Pyrazines / chemistry*
Pyrroles / chemical synthesis
Pyrroles / chemistry*
Rhodium / chemistry*
Silver / chemistry*
Triazoles / chemistry*

Substances

Azides
Pyrazines
Pyrroles
Triazoles
Silver
Rhodium