One-pot sequential diprop-2-ynylation and cycloaddition: An efficient synthesis of novel N,N-bis(1,2,3-triazol-4-yl) methylarylamines starting from primary amines

Abstract

A facile, one-pot synthesis strategy for the tertiary arylamines bearing N,N-bis(1,2,3-triazol-4-yl)methyl structure has been developed by sequential diprop-2-ynylation of primary amines with propargyl bromide in the presence of calcium hydride in DMF and [3 + 2] “click” cycloaddition with organic azides promoted by cupric acetate in the mixed DMF-H₂O media. This protocol provides some features, such as high efficiency and regioselectivity, easy operation, and moderate to good product yield (56–84%) with a wide substrate scope under mild conditions.

Graphical Abstract

KEYWORDS:

• Cycloaddition
• diprop-2-ynylation
• N,N-bis(1,2,3-triazol-4-yl) methylarylamines
• one-pot procedure

Acknowledgments

The authors thank Prof. J.-F. Zhao and Dr. Z.-M. Zhang for providing MS analytical services.

Additional information

Funding

Financial support from the National Natural Science Foundation of China [21762022], the Research Program of Jiangxi Province Department of Education [GJJ160289, GJJ170934], the Opening Foundation of National Research Center for Carbohydrate Synthesis [GJDTZX-KF-201414] and the Opening Foundation of Key Laboratory of Functional Small Organic Molecule of Ministry of Education [KLFS-KF-201411] is gratefully acknowledged.