A copper-catalyzed domino route toward purine-fused tricyclic derivatives.
Purine-fused tricyclic derivatives have been synthesized via a copper-catalyzed domino Michael/oxidative cross-coupling reaction between adenines and nitroolefins for the first time. With air as the oxidant, this method has high regioselectivity, which provides a new route for constructing purine-nucleoside-conjugated systems with two newly formed C–N bonds. Meanwhile, purine nucleosides with an exocyclic amino group could be obtained easily by simple reduction, which may lead to potential applications in fluorescence recognition of various bases in vivo.
Ming-Sheng
MS
Xie
Zhi-Liang
ZL
Chu
Hong-Ying
HY
Niu
Gui-Rong
GR
Qu
Hai-Ming
HM
Guo
D002384:Catalysis; D003300:Copper / Q000737:chemistry*; D015394:Molecular Structure; D011083:Polycyclic Compounds / Q000138:chemical synthesis* / Q000737:chemistry*; D011684:Purine Nucleosides / Q000138:chemical synthesis* / Q000737:chemistry*; D011687:Purines / Q000737:chemistry*
D011083:Polycyclic Compounds; D011684:Purine Nucleosides; D011687:Purines; D003300:Copper