Artikel: Synthesis of novel series of 3,5-disubstituted imidazo[1,2-d] [1,2,4]thiadiazoles involving SNAr and Suzuki–Miyaura cross-coupling reactions
RSC advances. 2022 Feb. 23, v. 12, no. 10
2022
Abstract: 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 SNAr reactivity toward tosyl ... ...
Abstract | 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 SNAr 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. |
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Schlagwörter | Lewis acids ; Suzuki reaction ; arylation ; iodination ; regioselectivity |
Sprache | Englisch |
Erscheinungsverlauf | 2022-0223 |
Umfang | p. 6303-6313. |
Erscheinungsort | The Royal Society of Chemistry |
Dokumenttyp | Artikel |
ISSN | 2046-2069 |
DOI | 10.1039/d1ra07208k |
Datenquelle | NAL Katalog (AGRICOLA) |
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