A Novel Synthetic Route to 3-Sulfenyl- and 3-Selenylindoles by n-Bu4NI-Induced Electrophilic Cyclization
- 1 December 2008
- journal article
- letter
- Published by American Chemical Society (ACS) in Organic Letters
- Vol. 11 (1), 173-176
- https://doi.org/10.1021/ol8021287
Abstract
3-Sulfenyl- and 3-selenylindoles are prepared in excellent yields by the palladium/copper-catalyzed crossing coupling of N,N-dialkyl-o-iodoanilines and terminal alkynes, followed by electrophilic cyclization with arylsulfenyl chlorides and arylselenyl chlorides in the presence of a stoichiometric amount of n-Bu4NI.Keywords
This publication has 34 references indexed in Scilit:
- Indole-3-carbinol as a chemopreventive and anti-cancer agentCancer Letters, 2008
- Human papillomavirus, cervical carcinogenesis and chemoprevention with Indole derivates - a review of pathomechanismsMolecular Nutrition & Food Research, 2007
- Arylthioindole Inhibitors of Tubulin Polymerization. 3. Biological Evaluation, Structure−Activity Relationships and Molecular Modeling StudiesJournal of Medicinal Chemistry, 2007
- Indole, a core nucleus for potent inhibitors of tubulin polymerizationMedicinal Research Reviews, 2006
- Design, Molecular Modeling, Synthesis, and Anti-HIV-1 Activity of New Indolyl Aryl Sulfones. Novel Derivatives of the Indole-2-carboxamideJournal of Medicinal Chemistry, 2006
- Development of a Novel, Highly Efficient Halide-Catalyzed Sulfenylation of IndolesOrganic Letters, 2006
- Leukotriene modifiers as potential therapeutics for cardiovascular diseaseNature Reviews Drug Discovery, 2005
- A Highly Efficient Procedure for 3-Sulfenylation of Indole-2-carboxylatesOrganic Letters, 2004
- Facile and Efficient Sulfenylation Method Using Quinone Mono-O,S-Acetals under Mild ConditionsThe Journal of Organic Chemistry, 2001
- A New Synthesis of 3-ArylthioindolesSynthesis, 1988