α,α-Dibromoketones as Synthetic Equivalents of α-Bromoketones for the Synthesis of Thiazolo[3,2-a]benzimidazoles

Title:α,α-Dibromoketones as Synthetic Equivalents of α-Bromoketones for the Synthesis of Thiazolo[3,2-a]benzimidazoles

Volume: 21 Issue: 2

Author(s): Ravi Kumar, Reshmi R Nair, Richa Prakash, Taeho Bae, Toshifumi Dohi*Om Prakash*

Affiliation:

• Graduate School of Pharmaceutical Sciences, Ritsumeikan University, 1-1-1 Nojihigashi, Kusatsu, Shiga, 525-8577, Japan

• Department of Chemistry, Kurukshetra University, Kurukshetra, 136 119, India

Abstract: Utilization of α,α-dihalocarbonyl compounds as synthetic equivalents to α-halocarbonyl compounds has been explored in the synthesis of a wide range of highly useful heterocycles and α- functionalized ketones. The continuously growing demand of α,α-dibromoketones, as highly reactive and mild synthetic precursors/intermediates, to carry out selective organic transformations, prompted us to investigate their potential application for the synthesis of thiazolo[3,2-a]benzimidazoles. In this study, a remarkable application of α,α-dibromoacetophenones 5a-g in the development of a facile protocol for the synthesis of thiazolo[3,2-a]benzimidazoles 4a-g by avoiding the use of lachrymatory α- haloketones is described. Although the mechanism for the debromination from the intermediate compound 6 under these conditions is not confirmed, possible pathways have been suggested.

Cite this article as:

Kumar Ravi, Nair R Reshmi, Prakash Richa, Bae Taeho, Dohi Toshifumi*, Prakash Om*, α,α-Dibromoketones as Synthetic Equivalents of α-Bromoketones for the Synthesis of Thiazolo[3,2-a]benzimidazoles, Letters in Organic Chemistry 2024; 21 (2) . https://dx.doi.org/10.2174/1570178620666230803123511