Synthesis of new 6-halogeno-imidazo[1,2-a]pyridines by SRN1 reactions

Abstract

New 2-chloromethyl-6-halogeno-imidazo[1,2-a]pyridines and 2-chloromethyl-6-halogeno-3-nitroimidazo[1,2-a]pyridines were prepared and reacted under experimental conditions of S RN 1 reactions with different sulfur and carbon centered nucleophiles to give new 6-halogeno-2-substituted-imidazo[1,2-a]pyridines and 6-halogeno-3-nitro-2-substituted-imidazo[1,2-a] pyridines in good yields. Only the chloromethyl group was found to be reactive under these experimental conditions.

An efficient aqueous microwave-assisted Suzuki–Miyaura cross-coupling reaction in the thiazole series

“…The last reaction which furnished compound 4 (with 92% yield) was adapted to microwave experimental conditions in water in order to avoid using DMSO as solvent, generally used to synthesize arylsulfonyl derivatives 33 through S RN 1 experimental conditions. The 4-tosylmethyl group was chosen because sulfones are well-known to be employed in many synthetic methodologies 34 and it can be used further for the preparation of various 4-substituted heterocycles.…”

Antikinetoplastid SAR study in 3-nitroimidazopyridine series: Identification of a novel non-genotoxic and potent anti-T. b. brucei hit-compound with improved pharmacokinetic properties

“…In order to explore the role of the sulfone moiety, an original 2-phenylthiomethyl derivative 7 was prepared from 1b by a substitution reaction with sodium thiophenolate, formed in situ with NaH in DMSO at RT (Scheme 3), according to a protocol that we previously reported [21].…”