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- Title
Regioselective Synthesis of 2,4-Substituted Pyrido[1′,2′:1,5]pyrazolo[3,4- d]pyrimidines through Sequential Pd-Catalyzed Arylation and S<sub>N</sub>Ar Reactions.
- Authors
Belaroussi, Rabia; El Hakmaoui, Ahmed; Akssira, Mohamed; Guillaumet, Gérald; Routier, Sylvain
- Abstract
The synthesis and regioselective functionalization of rare 2,4-disubstituted-pyrido[1′,2′:1,5]pyrazolo[3,4- d]pyrimidine derivatives is reported. C-4 aminations were performed by chlorine nucleophilic substitution SNAr reactions, and their efficiencies were compared with those for direct one-pot amide C-O activation with bromotripyrrolidinophosphonium hexafluorophosphate (PyBroP) as a reagent. The latter method was used to perform palladium-catalyzed C-4 (het)arylation. Finally, two C-4 amino and aryl derivatives were prepared on a large scale and engaged in desulfurative Liebeskind-Srogl-type reactions under microwave irradiation to afford the envisioned compound library. Each step was optimized, and the results are discussed.
- Subjects
ARYLATION; IRRADIATION; RADIATION; PALLADIUM; CHLORINE
- Publication
European Journal of Organic Chemistry, 2016, Vol 2016, Issue 21, p3550
- ISSN
1434-193X
- Publication type
Article
- DOI
10.1002/ejoc.201600356