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

J Tummatorn, C Thongsornkleeb…

Index: Tummatorn, Jumreang; Thongsornkleeb, Charnsak; Ruchirawat, Somsak; Gettongsong, Tanita Organic and Biomolecular Chemistry, 2013 , vol. 11, # 9 p. 1463 - 1467

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Citation Number: 15

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 ...