Chemical and Pharmaceutical Bulletin p. 1281 - 1286 (1995)
Update date:2022-08-04
Topics:
Murakami
Watanabe
Hagiwara
Akiyama
Ishii
The Fischer indolization of ethyl pyruvate 2-[2- (trifluoromethyl)phenyl]phenylhydrazone (5) gave two indolic products, ethyl 7-(trifluoromethyl)-1-phenylindole-2-carboxylate (12) as a minor product and ethyl 1-[2-(trifluoromethyl)phenyl]indole-2-carboxylate (13) as a major product. This result shows that the Fischer indolization occurred on the more electron-rich phenyl group. In the Goldberg reaction to prepare 13 from ethyl indole-2-carboxylate (15) and o- (21) or m-bromo-α,α,α-trifluorotoluene (23), it was found that Goldberg reaction proceeds via a benzyne mechanism, at least in part, in a sterically crowded situation.
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Doi:10.1016/j.tetlet.2014.10.005
(2014)Doi:10.1021/jm00023a007
(1995)Doi:10.1016/0040-4039(95)01515-9
(1995)Doi:10.1016/0022-328X(96)06143-8
(1996)Doi:10.1039/b814606c
(2009)Doi:10.1080/15257779508009744
(1995)
