10.1021/acs.orglett.7b02582.s002
Yuelei Gao
Yuelei
Gao
Zhongyan Hu
Zhongyan
Hu
Jinhuan Dong
Jinhuan
Dong
Jun Liu
Jun
Liu
Xianxiu Xu
Xianxiu
Xu
Chemoselective Double Annulation of Two Different
Isocyanides: Rapid Access to Trifluoromethylated Indole-Fused Heterocycles
American Chemical Society
2017
atom-economic strategy
acylaryl isocyanides
18 O-labeling experiment
indole
domino reaction
Rapid Access
chemoselective heterodimerization
Trifluoromethylated Indole-Fused Heterocycles
Chemoselective Double Annulation
Isocyanide insertion
Different Isocyanides
α- trifluoromethylated isocyanides
2017-09-13 18:35:20
Dataset
https://acs.figshare.com/articles/dataset/Chemoselective_Double_Annulation_of_Two_Different_Isocyanides_Rapid_Access_to_Trifluoromethylated_Indole-Fused_Heterocycles/5404606
An unprecedented chemoselective double
annulation of α-trifluoromethylated
isocyanides with <i>o</i>-acylaryl isocyanides has been
developed. This new reaction provides a rapid, efficient, and complete
atom-economic strategy for the synthesis of trifluoromethylated oxadiazino[3,2-<i>a</i>]indoles in a single operation from readily available starting
materials. Isocyanide insertion into CO double bonds is disclosed
for the first time as indicated by the results of <sup>18</sup>O-labeling
experiment. A mechanism for this domino reaction is proposed involving
chemoselective heterodimerization of two different isocyanides, followed
by indole-2,3-epoxide formation and rearrangement.