A facile synthesis of 4-azaisoindoles and their transformation into novel pyrrole-fused 2-pyridones

We describe herein a novel, efficient and practical synthetic approach to access pyrrolo[3,4-b]pyridines from dihydropyridones in three steps, in which a pyrrole unit is generated from a dihydropyridone using TosMIC reagent. Protection of the resulting pyrrole, Grignard addition followed by oxidativ...

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Bibliographic Details
Published in:Tetrahedron 2021-01, Vol.78, p.131807, Article 131807
Main Authors: Kiren, Sezgin, Grimes, Felicia, Mohammed, Hassan, Alazawi, Doaa
Format: Article
Language:English
Subjects:
Alkylation of pyrrolo[3,4-b]pyridines
Oxidation of pyrrolo[3,4-b]pyridinium salts
Oxidative aromatization
Pyrrole-fused 2-pyridones
Pyrrolo[3,4-b]pyridines
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Summary:We describe herein a novel, efficient and practical synthetic approach to access pyrrolo[3,4-b]pyridines from dihydropyridones in three steps, in which a pyrrole unit is generated from a dihydropyridone using TosMIC reagent. Protection of the resulting pyrrole, Grignard addition followed by oxidative aromatization afford substituted pyrrolo[3,4-b]pyridines. These underutilized structures are subsequently transformed to novel pyrrole-fused 2-pyridones via N-alkylation and then oxidation. [Display omitted] •Novel method to generate pyrrolopyridines.•Various R groups on pyrrolopyridines.•Novel salts from pyrrolopyridines.•Novel pyrrole-fused 2-pyridones.•Various groups on the pyrrole-fused 2-pyridones.
ISSN:0040-4020
1464-5416
DOI:10.1016/j.tet.2020.131807