Microwave-assisted Suzuki-Miyaura and Sonogashira coupling of 4-Chloro-2-(trifluoromethyl)pyrido[1,2-e]purine derivatives - CNRS - Centre national de la recherche scientifique Accéder directement au contenu
Article Dans Une Revue European Journal of Organic Chemistry Année : 2019

Microwave-assisted Suzuki-Miyaura and Sonogashira coupling of 4-Chloro-2-(trifluoromethyl)pyrido[1,2-e]purine derivatives

Synthèse de 4-Chloro-2-(trifluoromethyl)pyrido[1,2-e]purines et couplages de Suzuki-Miyaura et Sonogashira sous irradiations aux microondes

Résumé

The convenient preparation of three imidazo[1,2-a]pyridine-2-carboxamide intermediates is reported through known Strecker-Ugi type multicomponent reactions, Tschitschibabin type condensations and further synthetic sequences. The derivatives were then efficiently converted to novel 4-chloro-2-(trifluoromethyl)pyrido[1,2-e]purines by way of their original reactions with 2,2,2-trifluoroacetamide, followed by subsequent dehydroxychlorination reactions. These compounds were cross-coupled under microwave irradiation through Suzuki-Miyaura and Sonogashira palladium(0) catalysis to various aromatic and alkynyl reagents, thus providing the related C-4 substituted pyrido[1,2-e]purines of biological interest in good yields.
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Dates et versions

hal-02347523 , version 1 (05-11-2019)

Identifiants

Citer

Zahira Tber, Nicolas G. Biteau, Luigi Agrofoglio, Julien Cros, Stéphane Goffinont, et al.. Microwave-assisted Suzuki-Miyaura and Sonogashira coupling of 4-Chloro-2-(trifluoromethyl)pyrido[1,2-e]purine derivatives. European Journal of Organic Chemistry, 2019, 2019, pp.5756-5767. ⟨10.1002/ejoc.201900921⟩. ⟨hal-02347523⟩
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