Issue 11, 2003
From the journal:

New Journal of Chemistry

Wittig reactions of chromone-3-carboxaldehydes with benzylidenetriphenyl phosphoranes: a new synthesis of 3-styrylchromones

Angela Sandulache,a   Artur M. S. Silva,*a   Diana C. G. A. Pinto,a   Lúcia M. P. M. Almeidaa  and  José A. S. Cavaleiro*a  

* Corresponding authors

a Department of Chemistry, University of Aveiro, Aveiro, Portugal
E-mail: arturs@dq.ua.pt, jcavaleiro@dq.ua.pt
Fax: 351 234 370084

Abstract

An efficient route to 3-styrylchromones has been developed and applied to syntheses of several new derivatives. Wittig reactions of chromone-3-carboxaldehydes with some benzylic ylides gave a diastereomeric mixture of (E) and (Z)-3-styrylchromones that are separable by thin layer chromatography. The (Z)-isomers were the most abundant diastereomers independent of having electron-withdrawing or electron-donating substituents on the phenyl ring. Stereochemistry of the obtained diastereomers was established using NOESY experiments.

Graphical abstract: Wittig reactions of chromone-3-carboxaldehydes with benzylidenetriphenyl phosphoranes: a new synthesis of 3-styrylchromones

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Article information

DOI
https://doi.org/10.1039/B303554A
Article type
Paper
Submitted
28 Mar 2003
Accepted
05 Aug 2003
First published
03 Sep 2003

New J. Chem., 2003,27, 1592-1598

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Wittig reactions of chromone-3-carboxaldehydes with benzylidenetriphenyl phosphoranes: a new synthesis of 3-styrylchromones

A. Sandulache, A. M. S. Silva, D. C. G. A. Pinto, L. M. P. M. Almeida and J. A. S. Cavaleiro, New J. Chem., 2003, 27, 1592 DOI: 10.1039/B303554A

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