Premium
Microwave‐Assisted Suzuki–Miyaura and Sonogashira Coupling of 4‐Chloro‐2‐(trifluoromethyl)pyrido[1,2‐ e ]purine Derivatives
Author(s) -
Tber Zahira,
Biteau Nicolas G.,
Agrofoglio Luigi,
Cros Julien,
Goffit Stéphane,
Castaing Bertrand,
Nicolas Cyril,
Roy Vincent
Publication year - 2019
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201900921
Subject(s) - chemistry , sonogashira coupling , trifluoromethyl , reagent , purine metabolism , microwave irradiation , palladium , pyridine , purine , coupling reaction , combinatorial chemistry , catalysis , stereochemistry , organic chemistry , medicinal chemistry , alkyl , enzyme
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.