Synthesis of 2-Substituted-6,7-dimethoxy- and 6,7,8-Trimethoxy-3-hydroxyquinolin-4(1H)-ones

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Title:Synthesis of 2-Substituted-6,7-dimethoxy- and 6,7,8-Trimethoxy-3-hydroxyquinolin-4(1H)-ones
Creators:
Hradil, Pavel
Vaněček, Jan
Hlaváč, Jan
Ševčík, Juraj
Journal or Publication Title:
Collection of Czechoslovak Chemical Communications, 64, 2, pp. 257-264
Uncontrolled Keywords:Anthranilates, 3-Hydroxyquinolin-4(1<i>H</i>)-ones, Quinolinones, Cyclization

Abstract

Acetonyl and phenacyl esters of 4,5-dimethoxy- and 3,4,5-trimethoxyanthranilic acids <strong>3</strong> were prepared by reduction of corresponding nitro derivatives <strong>2</strong>. Acetonyl 4,5-dimethoxyanthranilate (<strong>3a</strong>) was prepared by reaction of 4,5-dimethoxyanthranilic acid and chloroacetone. Cyclization of these acetonyl and phenacyl esters in polyphosphoric acid provided the corresponding 2-substituted-6,7-dimethoxy- and 6,7,8-trimethoxy-3-hydroxyquinolin-4(1<i>H</i>)-ones <strong>4</strong>. A new method of the thermal cyclization is also described. The structure of the prepared compounds was confirmed by <sup>1</sup>H&nbsp;NMR spectroscopy. <p>

Title:Synthesis of 2-Substituted-6,7-dimethoxy- and 6,7,8-Trimethoxy-3-hydroxyquinolin-4(1H)-ones
Creators:
Hradil, Pavel
Vaněček, Jan
Hlaváč, Jan
Ševčík, Juraj
Uncontrolled Keywords:Anthranilates, 3-Hydroxyquinolin-4(1<i>H</i>)-ones, Quinolinones, Cyclization
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:64
Number:2
Page Range:pp. 257-264
ISSN:0010-0765
E-ISSN:1212-6950
Publisher:Institute of Organic Chemistry and Biochemistry
Related URLs:
URLURL Type
http://dx.doi.org/10.1135/cccc19990257UNSPECIFIED
ID Code:1474
Item Type:Article
Deposited On:06 Feb 2009 17:09
Last Modified:06 Feb 2009 16:09

Citation

Hradil, Pavel; Vaněček, Jan; Hlaváč, Jan; Ševčík, Juraj (1999) Synthesis of 2-Substituted-6,7-dimethoxy- and 6,7,8-Trimethoxy-3-hydroxyquinolin-4(1H)-ones. Collection of Czechoslovak Chemical Communications, 64 (2). pp. 257-264. ISSN 0010-0765

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