Direct Multicomponent Synthesis of C3-Arylated Pyrroles under Catalyst-Free Conditions

Amol Prakash Pawar; Reena Jangir; Atul Jankiram Dolas; Yadav Kacharu Nagare; Krishnan Rangan; Eldhose Iype; Indresh Kumar

doi:10.1055/a-2380-3855

Synthesis, Table of Contents

Synthesis 2025; 57(02): 380-388
DOI: 10.1055/a-2380-3855

paper

Special Topic Dedicated to Prof. H. Ila

Direct Multicomponent Synthesis of C3-Arylated Pyrroles under Catalyst-Free Conditions

Amol Prakash Pawar

^aDepartment of Chemistry, Birla Institute of Technology & Science, Pilani 333 031, India

,

Reena Jangir

^aDepartment of Chemistry, Birla Institute of Technology & Science, Pilani 333 031, India

,

Atul Jankiram Dolas

^aDepartment of Chemistry, Birla Institute of Technology & Science, Pilani 333 031, India

,

Yadav Kacharu Nagare

^aDepartment of Chemistry, Birla Institute of Technology & Science, Pilani 333 031, India

,

Krishnan Rangan

^bDepartment of Chemistry, BITS Pilani, Hyderabad Campus, Hyderabad 500078, Telangana, India

,

Eldhose Iype

^cCollege of Engineering and Technology, American University of the Middle East, Kuwait

,

Indresh Kumar∗

^aDepartment of Chemistry, Birla Institute of Technology & Science, Pilani 333 031, India

› Author Affiliations

Abstract

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Abstract

An operationally simple catalyst-free protocol for the direct regiospecific synthesis of C3-arylated/alkenylated pyrroles has been developed. The enamine-intermediate, in situ generated from succinaldehyde and a primary amine, was trapped with activated carbonyls before the Paal–Knorr reaction in a direct multicomponent ‘just-mix’ protocol to furnish pyrroles in good yields. Several C3-substituted N-alkylpyrroles have been prepared under open-flask conditions, avoiding protection-deprotection chemistry.

Key words

pyrrole - quinone - enamine - Paal–Knorr reaction - one-pot

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References

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18 CCDC 2222683 (7h) contains the supplementary crystallographic data for this paper. The data can be obtained free of charge from The Cambridge Crystallographic Data Centre via www.ccdc.cam.ac.uk/structures (for more details, see ESI)

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