Synthesis 2008(13): 2122-2126  
DOI: 10.1055/s-2008-1067114
PAPER
© Georg Thieme Verlag Stuttgart · New York

The First Synthesis of Bis(arylmethylidene)dioxan-5-ones: Potential Scaffolds to Access Vicinal Tricarbonyl Derivatives

M. Saeed Abaee*a, Mohammad M. Mojtahedi*a, Vahid Hamidia, A.Wahid Mesbaha, Werner Massab
a Organic Chemistry Department, Chemistry and Chemical Engineering Research Center of Iran, P.O. Box 14335-186, Tehran, Iran
b Fachbereich Chemie der Philipps-Universitaet Marburg, Hans-Meerwein-Strasse, 35032 Marburg, Germany
Fax: +98(21)44580762; e-Mail: abaee@ccerci.ac.ir; e-Mail: mojtahedi@ccerci.ac.ir;
Further Information

Publication History

Received 4 March 2008
Publication Date:
21 May 2008 (online)

Abstract

Double crossed-aldol condensation of a variety of aromatic aldehydes with 1,3-dioxan-5-one in the presence of magnesium bromide diethyl etherate and diethylamine at room temperature is described. Excellent yields of 4,6-bis(arylmethylidene)dioxan-5-ones are achieved in a facile, one-pot, general procedure. The structure and the Z,Z-configuration of the exocyclic double bonds of the products were determined by spectroscopic methods and X-ray crystallography, respectively.

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For an updated list of references on the preparation and synthetic applications of these compounds, see references 14-18 and references therein.