Cyclization of Phenacyl 2-{[2,2-Di(ethoxycarbonyl)vinyl]amino}benzoate

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Title:Cyclization of Phenacyl 2-{[2,2-Di(ethoxycarbonyl)vinyl]amino}benzoate
Creators:
Hradil, Pavel
Kvapil, Lubomír
Hlaváč, Jan
Lemr, Karel
Ševčík, Juraj
Journal or Publication Title:
Collection of Czechoslovak Chemical Communications, 63, 4, pp. 520-524
Uncontrolled Keywords:Phenacyl aminobenzoate, Thermal cyclization, Quinolones, Gould-Jacobs reaction

Abstract

Reaction of phenacyl anthranilate (<strong>1</strong>) with diethyl (ethoxymethylidene)malonate afforded phenacyl 2-{[2,2-di(ethoxycarbonyl)vinyl]amino}benzoate (<strong>2</strong>) which on heating in polyphosphoric acid underwent degradation. Thermal cyclization of <strong>2</strong> in diphenyl ether gave phenacyl 3-(ethoxycarbonyl)-4-oxo-1,4-dihydroquinoline-8-carboxylate (<strong>4</strong>). The phenacyl group did not cyclize even on prolonged heating at 250 °C. Heating in sulfuric acid resulted in hydrolysis of the ethyl ester under formation of 4-oxo-8-[(phenacyloxy)carbonyl]-1,4-dihydroquinoline-3-carboxylic acid (<strong>6</strong>). The structure of <strong>4</strong> was confirmed by an independent synthesis.

Title:Cyclization of Phenacyl 2-{[2,2-Di(ethoxycarbonyl)vinyl]amino}benzoate
Creators:
Hradil, Pavel
Kvapil, Lubomír
Hlaváč, Jan
Lemr, Karel
Ševčík, Juraj
Uncontrolled Keywords:Phenacyl aminobenzoate, Thermal cyclization, Quinolones, Gould-Jacobs reaction
Divisions:Life and Chemical Sciences > Institute of Organic Chemistry and Biochemistry > Collection of Czechoslovak Chemical Communications
Journal or Publication Title:Collection of Czechoslovak Chemical Communications
Volume:63
Number:4
Page Range:pp. 520-524
ISSN:0010-0765
E-ISSN:1212-6950
Publisher:Institute of Organic Chemistry and Biochemistry
Related URLs:
URLURL Type
http://dx.doi.org/10.1135/cccc19980520UNSPECIFIED
ID Code:1317
Item Type:Article
Deposited On:06 Feb 2009 17:08
Last Modified:06 Feb 2009 16:08

Citation

Hradil, Pavel; Kvapil, Lubomír; Hlaváč, Jan; Lemr, Karel; Ševčík, Juraj (1998) Cyclization of Phenacyl 2-{[2,2-Di(ethoxycarbonyl)vinyl]amino}benzoate. Collection of Czechoslovak Chemical Communications, 63 (4). pp. 520-524. ISSN 0010-0765

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