Catalyst-Free Construction of Imidazole-Pyrrolo[1,2-]pyrazine Hybrid, 2,6-Disubstituted Imidazo[1,2-]pyrrolo[2,1-]pyrazine via Regioselective Annulative Functionalizations.

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: December 2024

Highly efficient catalyst-free annulative functionalization approaches to a novel imidazole-pyrrolo[1,2-]pyrazine hybrid structure were devised from the reaction of β-enaminone with propargylamine where regioselective conjugate substitution of β-enaminone with propargylamine followed by cycloisomerization proceeded smoothly in a domino fashion to construct two heterocyclic moieties (pyrazine and imidazole) via successive formation of three C-N bonds, leading to the target tricyclic skeleton.

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http://dx.doi.org/10.1021/acs.joc.4c01576DOI Listing

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Catalyst-Free Construction of Imidazole-Pyrrolo[1,2-]pyrazine Hybrid, 2,6-Disubstituted Imidazo[1,2-]pyrrolo[2,1-]pyrazine via Regioselective Annulative Functionalizations.

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