Issue 7, 2001
From the journal:

Chemical Communications

Competitive intramolecular nucleophilic aromatic substitution: a new route to coumarins

Concepción Alonso,a   Marilyn M. Olmstead,a   Michael H. Nantza  and  Mark J. Kurth*a  

* Corresponding authors

a Department of Chemistry, University of California, One Shields Avenue, Davis, CA, USA.
E-mail: mjkurth@ucdavis.edu

Abstract

4-Hydroxy-3-(2′-pyridyl)coumarins (4) (R = 6-Cl, H, 6-NO2, 8-NO2) were prepared in moderate to good yields by the intramolecular nucleophilic aromatic substitution reaction of β-ketoesters (I) in refluxing xylenes; evidence for the reversible formation of benzo[c]quinolizinium III from I (X = 4-Cl), with eventual formation of 4 (R = 6-Cl), is also presented.

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Article information

DOI
https://doi.org/10.1039/B009172N
Article type
Feature Article
Submitted
10 Nov 2000
Accepted
17 Jan 2001
First published
14 Mar 2001

Chem. Commun., 2001, 639-640

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Competitive intramolecular nucleophilic aromatic substitution: a new route to coumarins

C. Alonso, M. M. Olmstead, M. H. Nantz and M. J. Kurth, Chem. Commun., 2001, 639 DOI: 10.1039/B009172N

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