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.4c01576 | DOI Listing |
J Org Chem
December 2024
College of Pharmacy and Yonsei Institute of Pharmaceutical Sciences, Yonsei University, 85 Songdogwahak-ro, Yeonsu-gu, Incheon 21983, Republic of Korea.
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.
View Article and Find Full Text PDFACS Chem Neurosci
September 2023
Department of Integrative Biotechnology & Translational Medicine, Yonsei University, 85 Songdogwahak-ro, Yeonsu-gu, Incheon 21983, South Korea.
Abnormal assembly of amyloid β (Aβ) in the brain is implicated in Alzheimer's disease (AD) and is associated with cognitive impairments. Since Aβ accumulation occurs in advance of the onset of clinical symptoms, identifying preventable drug candidates regulating Aβ accumulation is regarded as a promising approach in AD therapeutic. Herein, we synthesized eight Yonsei Institute of pharmaceutical sciences Alzheimer's Drug (YIAD) compounds based on 5-benzyl-6-phenylbenzo[4,5]imidazo[1,2-]pyrrolo[2,1-]pyrazine structures.
View Article and Find Full Text PDFRSC Adv
February 2020
College of Pharmacy, Yonsei Institute of Pharmaceutical Sciences, Yonsei University 85 Songdogwahak-ro, Yeonsu-gu Incheon 21983 Republic of Korea +82 32 749 4105 +82 32 749 4515.
A modular approach to polycyclic N-fused heteroaromatics is described. Acid-catalyzed reactions of various 1-(2-oxo-2-arylethyl)-1-pyrrole-2-carbaldehydes with several -phenylenediamines provided facile access to a number of new benzo[]imidazole-pyrrolo[1,2-]pyrazine hybrid structures through double cyclodehydration and aromatization. Optical characterization of the synthesized compounds revealed unique emission properties, with deep blue emission in the aggregated and solid states, and a dramatic substituent effect was observed.
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