Issue 2, 2024

Catalyst-free assembly of a polyfunctionalized 1,2,4-triazole-fused N-heterocycle, 6-acylated pyrrolo[1,2-a][1,2,4]triazolo[5,1-c]pyrazine

Abstract

A catalyst-free synthetic route to a new 1,2,4-triazole-pyrrolo[1,2-a]pyrazine hybrid system, 6-acylpyrrolo[1,2-a][1,2,4]triazolo[5,1-c]pyrazine, was realized upon sequential exposure of pyrrole-2-carbonitrile-derived substrates to DMF-DMA and acyl hydrazide through which acylated pyrazine and 1,2,4-triazole rings were consecutively formed with the formation of multiple bonds (one C–C bond and three C–N bonds). This annulative functionalization approach towards N-fused polycycles enabled us to install various substituents at specific positions on the core skeleton.

Graphical abstract: Catalyst-free assembly of a polyfunctionalized 1,2,4-triazole-fused N-heterocycle, 6-acylated pyrrolo[1,2-a][1,2,4]triazolo[5,1-c]pyrazine

Supplementary files

Article information

Article type
Paper
Submitted
25 Oct 2023
Accepted
29 Nov 2023
First published
29 Nov 2023

Org. Biomol. Chem., 2024,22, 320-336

Catalyst-free assembly of a polyfunctionalized 1,2,4-triazole-fused N-heterocycle, 6-acylated pyrrolo[1,2-a][1,2,4]triazolo[5,1-c]pyrazine

H. Oh and I. Kim, Org. Biomol. Chem., 2024, 22, 320 DOI: 10.1039/D3OB01747H

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