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- Title
Synthesis of New 2,3-Disubstituted 4-Chloro-1-hydroxyindoles.
- Authors
Park, Yeon Kyeong; Kim, Hyejin; Kim, Dong Sun; Cho, Hyunsung; Moon, Aree; Jeong, Choonsik; Yoon, Hye-Ran; Lee, Sang Hyup
- Abstract
The syntheses of new 2,3-disubstituted 4-chloro-1-hydroxyindoles were described. The conjugate nitro ketoester was reacted with various thiol and alcohol nucleophiles by the action of stannous chloride dihydrate through the unique processes of reduction of nitro group, intramolecular condensation, and addition of nucleophiles in one pot, to provide multisubstituted 1-hydroxyindoles. The reactions with thiol nucleophiles provided better results than those with alcohols, and, in particular, secondary and tertiary thiols provided best yields.
- Subjects
CHLORINE compounds; CHEMICAL synthesis; HETEROCYCLIC compounds synthesis; NUCLEOPHILIC reactions; NUCLEOPHILES; CONDENSATION reactions; THIOLS
- Publication
Bulletin of the Korean Chemical Society, 2015, Vol 36, Issue 8, p2095
- ISSN
0253-2964
- Publication type
Article
- DOI
10.1002/bkcs.10410