Issue 3, 2012
From the journal:

Green Chemistry

Domino reactions in water: diastereoselective synthesis of densely functionalized indolyldihydrofuran derivatives†

Pethaiah Gunasekaran,a   Kamaraj Balamurugan,a   Sathiyamoorthi Sivakumar,a   Subbu Perumal,*a   J. Carlos Menéndez*b  and  Abdulrahman I. Almansourc  

* Corresponding authors

a Department of Organic Chemistry, School of Chemistry, Madurai Kamaraj University, Madurai 625021, India
E-mail: subbu.perum@gmail.com
Fax: +91-452-2459845

b Departamento de Química Orgánica y Farmacéutica, Facultad de Farmacia, Universidad Complutense, 28040 Madrid, Spain
E-mail: josecm@farm.ucm.es
Fax: +34-91-3941822

c Department of Chemistry, College of Science, King Saud University, P.O. Box 2455, Riyadh 11451, Saudi Arabia

Abstract

A library of trans-5-aroyl-2-(indol-3-yl)-4-aryl-4,5-dihydrofuran-3-carbonitriles was diastereoselectively synthesized in excellent yields from the reaction of 2-(3-indolylcarbonyl)-3-aryl-2-propenenitriles with (2-aryl-2-oxoethyl)pyridinium bromides in the presence of triethylamine via a simple, user-friendly domino process carried out in water. Extraction and chromatographic steps were avoided, since the final products could be simply filtered from the aqueous reaction medium and recrystallized. This one-pot transformation generates one C–C and one C–O bond and presumably proceeds by a domino sequence involving the generation of a pyridinium ylide, a Michael addition and a final annulation via intramolecular nucleophilic substitution.

Graphical abstract: Domino reactions in water: diastereoselective synthesis of densely functionalized indolyldihydrofuran derivatives

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Article information

DOI
https://doi.org/10.1039/C2GC16517A
Article type
Paper
Submitted
25 Nov 2011
Accepted
27 Dec 2011
First published
23 Jan 2012

Green Chem., 2012,14, 750-757

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Domino reactions in water: diastereoselective synthesis of densely functionalized indolyldihydrofuran derivatives

P. Gunasekaran, K. Balamurugan, S. Sivakumar, S. Perumal, J. C. Menéndez and A. I. Almansour, Green Chem., 2012, 14, 750 DOI: 10.1039/C2GC16517A

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