Double isocyanide cyclization: a synthetic strategy for two-carbon-tethered pyrrole/oxazole pairs.
A new strategy for the construction of the compounds with two different heterocycles, linked by a C(2)-tether via a domino process involving [5 + 1] annulation, ring-opening, and subsequent double isocyanide cyclization, from the reaction of ethyl isocyanoacetate with divinyl ketones (DVKs) has been developed. The chemoselective fragmentation of the cyclohexanone intermediate is the key for the formation of not only the C(2)-tether but also the two different heterocycles.
Department of Chemistry, Northeast Normal University, Changchun 130024, China.
Yifei
Y
Li
Xianxiu
X
Xu
Jing
J
Tan
Chunyu
C
Xia
Dawei
D
Zhang
Qun
Q
Liu
D002244:Carbon / Q000737:chemistry*; D060326:Chemistry Techniques, Synthetic / Q000379:methods*; D003486:Cyanides / Q000737:chemistry*; D003500:Cyclization; D010080:Oxazoles / Q000737:chemistry*; D011758:Pyrroles / Q000737:chemistry*; D013379:Substrate Specificity
D003486:Cyanides; D010080:Oxazoles; D011758:Pyrroles; D002244:Carbon