Modular synthesis of pyrrole-fused heterocycles via glucose-mediated nitro-reductive cyclization

A novel biomass-derived glucose-mediated one-pot multicomponent nitro-reductive cyclization method is presented for the direct synthesis of diverse pyrrole-fused heterocycles. The process involves two-component reactions of alkyl (NH)-pyrrole-2-carboxylates and 2-fluoronitroarenes, yielding pyrrolo[...

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Bibliographic Details
Published in:Organic & biomolecular chemistry 2024-07, Vol.22 (28), p.5790-5796
Main Authors: Panday, Surabhi, Hazra, Amitava, Gupta, Pankaj, Manna, Srimanta, Laha, Joydev K
Format: Article
Language:English
Subjects:
Biomass
Carbon sources
Carboxylates
Chemical synthesis
Glucose
Green chemistry
Medical innovations
Pyrroles
Quinoxaline
Quinoxalines
Substrates
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Summary:A novel biomass-derived glucose-mediated one-pot multicomponent nitro-reductive cyclization method is presented for the direct synthesis of diverse pyrrole-fused heterocycles. The process involves two-component reactions of alkyl (NH)-pyrrole-2-carboxylates and 2-fluoronitroarenes, yielding pyrrolo[1,2- ]quinoxalin-4(5 )-ones, as well as three-component reactions utilizing (NH)-pyrroles, nitroarenes, and DMSO as carbon sources, resulting in various pyrrolo[1,2- ]quinoxaline derivatives. High yields were achieved with broad substrate scope and gram-scale synthesis capability, including pharmaceuticals featuring pyrroloquinoxaline scaffolds. The method's key innovation lies in enabling three or four reactions in a single-pot setup, previously unexplored in pyrrole chemistry. The simplicity of nitro group reduction by biomass-derived glucose ensures practical safety during scale-up, while mechanistic insights from control experiments reveal a new paradigm in pyrrole chemistry. The tandem process demonstrates low PMI values and high step and atom economies, aligning well with green chemistry principles.
ISSN:1477-0520
1477-0539
1477-0539
DOI:10.1039/d4ob00741g