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Iodine-Promoted C–H Bond Amination Reaction for the Synthesis of Fused Tricyclic Heteroarenes

Year: 2024

Type: article

Abstract: High Resolution Image Download MS PowerPoint Slide Fused heterocyclic scaffolds, such as benzimidazoles or larger ring systems containing a benzimidazole fragment, are frequently encountered in pharmaceutical compounds and other biologically active molecules. While there are many examples of N9- and/or C3-substituted 9 H -benzo[4,5]imidazo[2,1- c ][1,2,4]triazoles, current examples of the regioselective preparation of N1-substituted 1 H -benzo[4,5]imidazo[2,1- c ][1,2,4]triazoles are limited to N1-aryl substituted compounds, which also contain a C3-substituent. Here, we report an iodine-promoted C–H bond amination reaction that allows the selective preparation of 1 H -benzo[4,5]imidazo[2,1- c ][1,2,4]triazoles with a variety of aryl and alkyl N1-substituents. Not only do these cyclization reactions allow access to a new substitution pattern on the benzo[4,5]imidazo[2,1- c ][1,2,4]triazole scaffold, but they are also tolerant toward a wide range of functional groups, including esters, amides, alcohols, alkynes, and alkenes. Our findings expand the synthetic toolbox for the preparation of nitrogen containing fused heteroarenes.

Source: The Journal of Organic Chemistry

DOI: 10.1021/acs.joc.4c02282

Authors: Rachel E. Crittell, Rehema Nakiwala, Margaux J. Lavenue, Scott M. Hutchinson, Jeanne L. Bolliger

Institution: Oklahoma State University

Language: English

Topic: Catalytic C–H Functionalization Methods

Subfield: Organic Chemistry

Field: Chemistry

Domain: Physical Sciences

Open Access status: hybrid

Estimated APC paid: $4,500

Funder: Oklahoma State University