Chemoselective Double Annulation of Two Different
Isocyanides: Rapid Access to Trifluoromethylated Indole-Fused Heterocycles
Posted on 2017-09-13 - 18:35
An unprecedented chemoselective double
annulation of α-trifluoromethylated
isocyanides with o-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-a]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 18O-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.
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Gao, Yuelei; Hu, Zhongyan; Dong, Jinhuan; Liu, Jun; Xu, Xianxiu (2017). Chemoselective Double Annulation of Two Different
Isocyanides: Rapid Access to Trifluoromethylated Indole-Fused Heterocycles. ACS Publications. Collection. https://doi.org/10.1021/acs.orglett.7b02582
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AUTHORS (5)
YG
Yuelei Gao
ZH
Zhongyan Hu
JD
Jinhuan Dong
JL
Jun Liu
XX
Xianxiu Xu