Tuning the Annulation Reactivity of Vinyl Azides and Carbazates: A Divergent Synthesis of Aza-pyrimidinones and Imidazoles.
A divergent cascade annulation has been developed using readily available vinyl azides and carbazates with a wide range of substituents. Vinyl azides were successfully applied as bifunctional partners to prepare aza-pyrimidinones via 6-ring closure with carbazates as well as to construct polyfunctionalized imidazoles via 5-ring closure with N-substituted carbazates. The aza-heterocycles were obtained with high levels of chemoselectivity and excellent yields.
Zhejiang Province Key Laboratory of Anti-Cancer Drug Research, College of Pharmaceutical Science, Zhejiang University , Hangzhou 310058, P. R. China.
Jiaan
J
Shao
Zhejiang Province Key Laboratory of Anti-Cancer Drug Research, College of Pharmaceutical Science, Zhejiang University , Hangzhou 310058, P. R. China.
Xingyu
X
Liu
Zhejiang Province Key Laboratory of Anti-Cancer Drug Research, College of Pharmaceutical Science, Zhejiang University , Hangzhou 310058, P. R. China.
Ke
K
Shu
Zhejiang Province Key Laboratory of Anti-Cancer Drug Research, College of Pharmaceutical Science, Zhejiang University , Hangzhou 310058, P. R. China.
Pai
P
Tang
Zhejiang Province Key Laboratory of Anti-Cancer Drug Research, College of Pharmaceutical Science, Zhejiang University , Hangzhou 310058, P. R. China.
Jing
J
Luo
Zhejiang Province Key Laboratory of Anti-Cancer Drug Research, College of Pharmaceutical Science, Zhejiang University , Hangzhou 310058, P. R. China.
Wenteng
W
Chen
Zhejiang Province Key Laboratory of Anti-Cancer Drug Research, College of Pharmaceutical Science, Zhejiang University , Hangzhou 310058, P. R. China.
Yongping
Y
Yu
D001386:Azides / Q000737:chemistry*; D002384:Catalysis; D006834:Hydrazines / Q000737:chemistry*; D007093:Imidazoles / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D011744:Pyrimidinones / Q000138:chemical synthesis* / Q000737:chemistry
D001386:Azides; D006834:Hydrazines; D007093:Imidazoles; D011744:Pyrimidinones; C010877:carbazic acid