TiCl4/Et3N-promoted three-component condensation between aromatic heterocycles, aldehydes, and active methylene compounds

Andrea Renzetti; Emmanuel Dardennes; Antonella Fontana; Paolo De Maria; Janos Sapi; Stéphane Gérard

doi:10.1021/jo800529q

TiCl4/Et3N-promoted three-component condensation between aromatic heterocycles, aldehydes, and active methylene compounds

J Org Chem. 2008 Sep 5;73(17):6824-7. doi: 10.1021/jo800529q. Epub 2008 Aug 9.

Authors

Andrea Renzetti¹, Emmanuel Dardennes, Antonella Fontana, Paolo De Maria, Janos Sapi, Stéphane Gérard

Affiliation

¹ Institut de Chimie Moléculaire de Reims, UMR CNRS 6229, Université de Reims-Champagne-Ardenne, Faculté de Pharmacie, 51 rue Cognacq-Jay, F-51096 Reims, Cedex, France.

PMID: 18690741
DOI: 10.1021/jo800529q

Abstract

A one-pot methodology for the synthesis of polyfunctionalized indole derivatives by a TiCl4/Et3N-promoted trimolecular condensation of aldehydes, indole heterocycles, and various activated carbonyl compounds is reported. Rationalization of these reactions and extension to other heterocyclic systems is also described.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Aldehydes / chemistry*
Ethylamines / chemistry*
Heterocyclic Compounds / chemistry*
Indoles / chemical synthesis*
Methane / chemistry*
Models, Chemical
Polycyclic Aromatic Hydrocarbons / chemistry*
Titanium / chemistry*

Substances

Aldehydes
Ethylamines
Heterocyclic Compounds
Indoles
Polycyclic Aromatic Hydrocarbons
titanium tetrachloride
Titanium
Methane