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
a   Department of Chemistry, Birla Institute of Technology & Science, Pilani 333 031, India
,
Reena Jangir
a   Department of Chemistry, Birla Institute of Technology & Science, Pilani 333 031, India
,
Atul Jankiram Dolas
a   Department of Chemistry, Birla Institute of Technology & Science, Pilani 333 031, India
,
Yadav Kacharu Nagare
a   Department of Chemistry, Birla Institute of Technology & Science, Pilani 333 031, India
,
Krishnan Rangan
b   Department of Chemistry, BITS Pilani, Hyderabad Campus, Hyderabad 500078, Telangana, India
,
Eldhose Iype
c   College of Engineering and Technology, American University of the Middle East, Kuwait
,
Indresh Kumar
a   Department of Chemistry, Birla Institute of Technology & Science, Pilani 333 031, India
› Author Affiliations
The authors acknowledge the financial support by DST-SERB, New Delhi (CRG/2020/003424) for this work.


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.

Supporting Information



Publication History

Received: 05 June 2024

Accepted after revision: 05 August 2024

Accepted Manuscript online:
05 August 2024

Article published online:
04 September 2024

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