Microwave‐Assisted Suzuki–Miyaura and Sonogashira Coupling of 4‐Chloro‐2‐(trifluoromethyl)pyrido[1,2‐e]purine Derivatives

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‐(trifl...

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Bibliographic Details
Published in:European journal of organic chemistry 2019-09, Vol.2019 (33), p.5756-5767
Main Authors: Tber, Zahira, Biteau, Nicolas G., Agrofoglio, Luigi, Cros, Julien, Goffinont, Stéphane, Castaing, Bertrand, Nicolas, Cyril, Roy, Vincent
Format: Article
Language:English
Subjects:
Base excision repair
Catalysis
Chemical Sciences
Cross‐coupling
C–C coupling
Fused‐ring systems
Nitrogen heterocycles
Organic chemistry
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Summary: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 their original reactions with 2,2,2‐trifluoroacetamide, followed by subsequent dehydroxychlorination reactions. These compounds were cross‐coupled under microwave irradiation through SuzukiMiyaura 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. The convenient preparation of novel 4‐chloro‐2‐(trifluoromethyl)pyrido[1,2‐e]purines by the original reactions of imidazo[1,2‐a]pyridine‐2‐carboxamides and 2,2,2‐trifluoroacetamide is reported. The derivatives were then efficiently cross‐coupled through Suzuki–Miyaura and Sonogashira catalysis to give the related C‐4 substituted pyrido[1,2‐e]purines of biological interest in good yields.
ISSN:1434-193X
1099-0690
DOI:10.1002/ejoc.201900921