Regioselective Access to 1,2,4-Triazole-Fused -Heterocycle, Pyrrolo[1,2-][1,2,4]triazolo[5,1-]pyrazine, via Double Dehydrative Cyclizations.

J Org Chem

College of Pharmacy and Yonsei Institute of Pharmaceutical Sciences, Yonsei University, 85 Songdogwahak-ro, Yeonsu-gu, Incheon 21983, Republic of Korea.

Published: August 2023

A highly efficient and regioselective approach to a novel 1,2,4-triazole-fused -heterocyclic scaffold, pyrrolo[1,2-][1,2,4]triazolo[3,4-]pyrazine, was established by base-promoted reaction of pyrrole-2-carbonitrile-derived substrate with acyl hydrazide where domino double ring closures comprised of enamine formation, attack on nitrile, and cyclodehydration enabled sequential construction of pyrazine and 1,2,4-triazole ring systems with formation of three C-N bonds.

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http://dx.doi.org/10.1021/acs.joc.3c01044DOI Listing

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