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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

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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… Click to show full abstract

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: sequential diprop; primary amines; bis triazol; diprop ynylation; one pot

Journal Title: Synthetic Communications
Year Published: 2019

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