Convenient Synthesis of 4-Alkyl, Alkenyl, and Alkynyl Substituted N-(Phenylsulfonyl)indoles

Hiroyuki ISHIBASHI; Susumu AKAMATSU; Hiroko IRIYAMA; Masazumi IKEDA

doi:10.1248/cpb.42.2150

Hiroyuki ISHIBASHI, Susumu AKAMATSU, Hiroko IRIYAMA, Masazumi IKEDA

Author information

Keywords: 4-alkylindole, 4-alkenylindole, 4-alkynylindole, Grignard reagent, organolithium compound, cupric chloride

JOURNAL FREE ACCESS

1994 Volume 42 Issue 10 Pages 2150-2153

DOI https://doi.org/10.1248/cpb.42.2150

Details

Abstract

The indolone 1 reacted with organomagnesium or lithium reagents to give the carbinols 6 and 10, which, upon treatment under appropriate acidic conditions or neutral thermal conditions, gave the 1-phenylsulfonylindoles 8 and 11 bearing various kinds of alkyl, alkenyl, and alkynyl substituents at the 4-position. The indolone 1 was also converted to the 4-cyanoindole 14 via the cyanohydrin O-trimethylsilyl ether 13.

Corresponding author

Register with J-STAGE for free!