Issue 9, 2013
From the journal:

Organic & Biomolecular Chemistry

Synthesis of 2,4-unsubstituted quinoline-3-carboxylic acid ethyl esters from arylmethyl azides via a domino process†

Jumreang Tummatorn,*a   Charnsak Thongsornkleeb,ab   Somsak Ruchirawatab  and  Tanita Gettongsonga  

* Corresponding authors

a Chulabhorn Research Institute, 54 Kamphaeng Phet 6, Laksi, Bangkok 10210, Thailand
E-mail: jumreang@cri.or.th
Fax: +66 2 574 0622
Tel: +66 2 574 0622 ext 1513

b Program on Chemical Biology, Chulabhorn Graduate Institute, Center of Excellence on Environmental Health and Toxicology, CHE, Ministry of Education, 54 Kamphaeng Phet 6, Laksi, Bangkok 10210, Thailand

Abstract

A convenient synthesis of 2,4-unsubstituted quinoline-3-carboxylic acid ethyl esters via a domino process is described. The synthesis employs arylmethyl azides as the precursor which undergoes an acid-promoted rearrangement to give an N-aryl iminium ion. Following the addition with ethyl 3-ethoxyacrylate, intramolecular electrophilic aromatic substitution, elimination and subsequent oxidation, the quinoline products were obtained in moderate to excellent yields.

Graphical abstract: Synthesis of 2,4-unsubstituted quinoline-3-carboxylic acid ethyl esters from arylmethyl azides via a domino process

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Article information

DOI
https://doi.org/10.1039/C3OB27493D
Article type
Communication
Submitted
23 Dec 2012
Accepted
16 Jan 2013
First published
18 Jan 2013

Org. Biomol. Chem., 2013,11, 1463-1467

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Synthesis of 2,4-unsubstituted quinoline-3-carboxylic acid ethyl esters from arylmethyl azides via a domino process

J. Tummatorn, C. Thongsornkleeb, S. Ruchirawat and T. Gettongsong, Org. Biomol. Chem., 2013, 11, 1463 DOI: 10.1039/C3OB27493D

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