Oxidative Cyclization of Amino Alcohols Catalyzed by a Cp*Ir Complex. Synthesis of Indoles, 1,2,3,4-Tetrahydroquinolines, and 2,3,4,5-Tetrahydro-1-benzazepine
- 13 July 2002
- journal article
- letter
- Published by American Chemical Society (ACS) in Organic Letters
- Vol. 4 (16) , 2691-2694
- https://doi.org/10.1021/ol026200s
Abstract
A new iridium-catalyzed oxidative cyclization of amino alcohols has been revealed. Indole derivatives are synthesized in good to excellent yields from 2-aminophenethyl alcohols by means of a [Cp*IrCl2]2/K2CO3 catalytic system. The present catalytic system is also effective for syntheses of 1,2,3,4-tetrahydroquinolines from 3-(2-aminophenyl)propanols and 2,3,4,5-tetrahydro-1-benzazepine from 4-(2-aminophenyl)butanol.Keywords
This publication has 9 references indexed in Scilit:
- Oxidation of primary and secondary alcohols catalyzed by a pentamethylcyclopentadienyliridium complexJournal of Organometallic Chemistry, 2002
- A practical one-pot synthesis of 2,3-disubstituted indoles from unactivated anilinesTetrahedron Letters, 2001
- Ruthenium-catalyzed heteroannulation of anilines with alkanolammonium chlorides leading to indolesTetrahedron, 2001
- Recent developments in indole ring synthesis—methodology and applicationsJournal of the Chemical Society, Perkin Transactions 1, 2000
- Synthesis of aromatic heterocyclesJournal of the Chemical Society, Perkin Transactions 1, 1999
- Facile and efficient synthesis of pyrroles and indoles via palladium-catalyzed oxidation of hydroxy-enamines and -aminesTetrahedron Letters, 1996
- Recent progress in the synthesis of 1,2,3,4,-tetrahydroquinolinesTetrahedron, 1996
- Palladium-catalyzed annulation of 1,4-dienes using ortho-functionally-substituted aryl halidesThe Journal of Organic Chemistry, 1993
- Transition Metals in the Synthesis and Functionalization of Indoles [New Synthesis Methods (72)]Angewandte Chemie International Edition in English, 1988