Rongalite-Promoted One-Pot Reductive Cyclization Strategy for the Construction of Pyrrolo[1,2-α]quinoxalines from 1-(2-Nitrophenyl)pyrroles

Abstract A transition-metal-free strategy for the synthesis of pyrrolo[1,2-α]quinoxalines and 7-methylindolo[1,2-α]quinoxaline from 1-(2-nitrophenyl)-1H-pyrrole or 3-methyl-1-(2-nitrophenyl)-1H-indole using rongalite have been developed. In this transformation, rongalite serves a dual function, acting as both a reducing agent and a one-carbon (C1) synthon. The method offers an alternative approach to C–N bond formation. Furthermore, to investigate the reaction mechanism, several control experiments were performed, including radical scavenger studies, formaldehyde detection experiments, and reduction studies. The method is readily scalable and enables further modification.

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Publication Details

Journal
The Journal of Organic Chemistry
Published
2026-09-29
DOI
https://doi.org/10.1021/acs.joc.6c01671
Primary Topic
Synthesis and Characterization of Pyrroles
Type
article
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article

Rongalite-Promoted One-Pot Reductive Cyclization Strategy for the Construction of Pyrrolo[1,2-α]quinoxalines from 1-(2-Nitrophenyl)pyrroles

Umesh A. Kshirsagar, Shivaji V. Surve, Pandurang B. Hardas
The Journal of Organic Chemistry
Synthesis and Characterization of Pyrroles
article

Rongalite-Promoted One-Pot Reductive Cyclization Strategy for the Construction of Pyrrolo[1,2-α]quinoxalines from 1-(2-Nitrophenyl)pyrroles

Umesh A. Kshirsagar, Shivaji V. Surve, Pandurang B. Hardas
article en

Abstract

Abstract A transition-metal-free strategy for the synthesis of pyrrolo[1,2-α]quinoxalines and 7-methylindolo[1,2-α]quinoxaline from 1-(2-nitrophenyl)-1H-pyrrole or 3-methyl-1-(2-nitrophenyl)-1H-indole using rongalite have been developed. In this transformation, rongalite serves a dual function, acting as both a reducing agent and a one-carbon (C1) synthon. The method offers an alternative approach to C–N bond formation. Furthermore, to investigate the reaction mechanism, several control experiments were performed, including radical scavenger studies, formaldehyde detection experiments, and reduction studies. The method is readily scalable and enables further modification.

The Journal of Organic Chemistry
Indian Institute of Technology Indore (IN)
Openalex Percentile: Top 22%
Synthesis and Characterization of Pyrroles
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