Metal-free [2 + 1 + 3] Cycloaddition of Trifluoroacetaldehyde N-Sulfonylhydrazones with Hexahydro-1,3,5-triazines Leading to Trifluoromethylated 2,3,4,5-Tetrahydro-1,2,4-triazines

Zhongxue Fang; Qihao Jin; Xinyu Wang; Yongquan Ning

doi:10.1021/acs.joc.1c02810

Metal-free [2 + 1 + 3] Cycloaddition of Trifluoroacetaldehyde N-Sulfonylhydrazones with Hexahydro-1,3,5-triazines Leading to Trifluoromethylated 2,3,4,5-Tetrahydro-1,2,4-triazines

J Org Chem. 2022 Mar 4;87(5):2966-2974. doi: 10.1021/acs.joc.1c02810. Epub 2022 Feb 8.

Authors

Zhongxue Fang¹, Qihao Jin¹, Xinyu Wang², Yongquan Ning²

Affiliations

¹ School of Chemistry and Environmental Engineering, Yancheng Teachers University, Yancheng 224007, China.
² Jilin Province Key Laboratory of Organic Functional Molecular Design & Synthesis, Department of Chemistry, Northeast Normal University, Changchun 130024, China.

PMID: 35133818
DOI: 10.1021/acs.joc.1c02810

Abstract

A transition-metal-free [2 + 1 + 3] cycloaddition of trifluoroacetaldehyde N-sulfonylhydrazone and hexahydro-1,3,5-triazine was described. This operationally simple protocol provides a general synthesis of diverse trifluoromethylated 2,3,4,5-tetrahydro-1,2,4-triazines in 81-97% yield with a broad substrate scope, including aryl, benzyl, and alkyl hexahydro-1,3,5-triazine.

Publication types

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

MeSH terms

Acetaldehyde* / analogs & derivatives
Cycloaddition Reaction
Metals
Triazines*

Substances

Metals
Triazines
trifluoroacetaldehyde
Acetaldehyde