Domino Cyclization Reaction of o-Diisocyanoarenes for the Synthesis of Imidazo[1,2-a]pyridinobenzimidazole Backbones

Mohammad Rezaei-Gohar, Kamran Amiri, Kimia Aghaie, Behrouz Nayebzadeh, Alireza Ariafard, Farshad Shiri, Frank Rominger, Dmitry Dar’in, Mikhail Krasavin*, Saeed Balalaie*

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

3 Citations (Scopus)

Abstract

An efficient procedure to access a variety of connected imidazo[1,2-a]pyridine and benzimidazole skeletons through the C-N bond was described as a new type of Buchwald-Hartwig reaction. Furthermore, the bis(imidazo[1,2-a]pyridin-3-yl)aryl-1,2-diamine scaffolds were obtained by changing the equivalent ratio of the starting materials. Some advantages of the protocol are the formation of four new bonds (C═C, C-N), a transition-metal-free reaction, a broad substrate scope, high yields, and mild reaction conditions. The reaction mechanism was confirmed on the basis of DFT calculations.

Original languageEnglish
Pages (from-to)5682-5686
Number of pages5
JournalOrganic Letters
Volume25
Issue number30
DOIs
Publication statusPublished - 4 Aug 2023
Externally publishedYes

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