Synthesis of novel series of 3,5-disubstituted imidazo[1,2- \textitd ] [1,2,4]thiadiazoles involving S _\textrmN Ar and Suzuki–Miyaura cross-coupling reactions - Archive ouverte HAL Access content directly
Journal Articles RSC Advances Year : 2022

Synthesis of novel series of 3,5-disubstituted imidazo[1,2- \textitd ] [1,2,4]thiadiazoles involving S _\textrmN Ar and Suzuki–Miyaura cross-coupling reactions

(1) , (1) , (1, 2) , (1) , (2) , (1) , (1)
1
2

Abstract

A convenient design of 3,5-disubstituted imidazo[1,2- d ][1,2,4]thiadiazoles is reported from 2-mercaptoimidazole, which afforded a versatile platform that was then used to access a variety of original heterocycles. , The first access to 3,5-disubstituted imidazo[1,2- d ][1,2,4]thiadiazole derivatives is reported. The series were generated from 2-mercaptoimidazole, which afforded the key intermediate bearing two functional positions. The S N Ar reactivity toward tosyl release at the C-3 position was investigated and a regioselective electrophilic iodination in C-5 position was performed to allow a novel C–C bond using Suzuki–Miyaura reaction. Palladium-catalyzed cross-coupling conditions were optimized. A representative library of various boronic acids was employed to establish the scope and limitations of the method. To complete this methodological study, the influence of the nature of the C-3 imidazo[1,2- d ][1,2,4]thiadiazole substitutions on the arylation in C-5 was investigated.

Dates and versions

hal-03890856 , version 1 (08-12-2022)

Identifiers

Cite

Clémentine Pescheteau, Matthieu Place, Alexandru Sava, Lea Nunes, Lenuta Profire, et al.. Synthesis of novel series of 3,5-disubstituted imidazo[1,2- \textitd ] [1,2,4]thiadiazoles involving S _\textrmN Ar and Suzuki–Miyaura cross-coupling reactions. RSC Advances, 2022, 12 (10), pp.6303--6313. ⟨10.1039/D1RA07208K⟩. ⟨hal-03890856⟩
0 View
0 Download

Altmetric

Share

Gmail Facebook Twitter LinkedIn More