BCl3-Mediated C-N, C-S, and C-O Bond Formation of Imidazo[1,2- a]pyridine Benzylic Ethers

Davinder Singh; Gulshan Kumar; Divya Dheer; Jyoti; Manoj Kushwaha; Qazi Naveed Ahmed; Ravi Shankar

doi:10.1021/acsomega.9b00035

BCl₃-Mediated C-N, C-S, and C-O Bond Formation of Imidazo[1,2- a]pyridine Benzylic Ethers

ACS Omega. 2019 Mar 1;4(3):4530-4539. doi: 10.1021/acsomega.9b00035. eCollection 2019 Mar 31.

Authors

Davinder Singh¹, Gulshan Kumar¹, Divya Dheer^{1

2}, Jyoti¹, Manoj Kushwaha¹, Qazi Naveed Ahmed¹, Ravi Shankar^{1

2}

Affiliations

¹ Bio-Organic Chemistry Division, Medicinal Chemistry Division, and Quality Control and Quality Assurance (QC & QA), CSIR-Indian Institute of Integrative Medicine, Jammu 180001, India.
² Academy of Scientific and Innovative Research (AcSIR), Jammu 180001, India.

Abstract

An efficient BCl₃-mediated reaction of imidazo[1,2-a]pyridines has been developed for the C-N, C-S, and C-O bond formation. The salient features of this method correspond to the substitution of different nucleophiles via in situ unconventional debenzylation. The developed process is applicable for the synthesis of a wide variety of ((3-amino/thio/alkoxy)-methyl)-imidazo[1,2-a]pyridines.