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

doi:10.1021/acs.joc.0c00712

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

Research output: Contribution to journal › Article › peer-review

29 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 language	English (US)
Pages (from-to)	6697-6708
Number of pages	12
Journal	Journal of Organic Chemistry
Volume	85
Issue number	10
DOIs	https://doi.org/10.1021/acs.joc.0c00712
State	Published - May 15 2020
Externally published	Yes

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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10.1021/acs.joc.0c00712

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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.",

author = "Jagadeshwar Vannada and Mahesh Sulthan and Doma Arun and Ravikrishna Dada and Srinivasarao Yaragorla",

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 {\textcopyright} 2020 American Chemical Society.",

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doi = "10.1021/acs.joc.0c00712",

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AU - Vannada, Jagadeshwar

AU - Sulthan, Mahesh

AU - Arun, Doma

AU - Dada, Ravikrishna

AU - Yaragorla, Srinivasarao

N1 - 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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Y1 - 2020/5/15

N2 - 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.

AB - 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.

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

Abstract

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