Regiodivergent Synthesis of Penta-Substituted Pyrroles through a Cascade [3 + 2] Cyclization of C-Acylimines with Activated Alkynes and Aromatic Nucleophiles

Jagadeshwar Vannada, Mahesh Sulthan, Doma Arun, Ravikrishna Dada, Srinivasarao Yaragorla

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19 Scopus citations

Abstract

Highly robust one-pot, four-component cascade cyclization reaction of α-keto aldehydes, anilines, activated alkynes, and aromatic nucleophiles is developed to synthesize a diverse range of pharmaceutically important penta-substituted pyrroles. The reaction proceeds through the cascade cyclization of acylimines (in situ formed) with activated alkynes and aromatic nucleophiles such as indoles, pyrroles, and naphthols at room temperature under calcium(II) catalysis with high yields and broad substrate diversity.

Original languageEnglish (US)
Pages (from-to)6697-6708
Number of pages12
JournalJournal of Organic Chemistry
Volume85
Issue number10
DOIs
StatePublished - May 15 2020
Externally publishedYes

Bibliographical note

Funding Information:
S.Y. is thankful to SERB, India, for funding through project no-2016/4812. MS and DA are thankful to CSIR, India, for their fellowships. MS is grateful to UGC-NRC facility at the School of Chemistry, University of Hyderabad.

Publisher Copyright:
Copyright © 2020 American Chemical Society.

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