Some reactions of N-propadienyl-4-quinolones

[img]PDF - Authorized users only
Language: English
246Kb
Title:Some reactions of N-propadienyl-4-quinolones
Creators:
Rádl, Stanislav
Kovářová, Lenka
Journal or Publication Title:
Collection of Czechoslovak Chemical Communications, 56, 11, pp. 2413-2419

Abstract

N-Alkylation of ethyl 6,7,8-trifluoro-1,4-dihydro-4-oxoquinoline-3-carboxylate (<i>Vg</i>) with 3-bromopropyne followed by acidic hydrolysis provided N-propyl derivative <i>Ic</i> which in alkaline media yielded N-propadienyl derivative <i>IId</i>. Propadienyl derivatives <i>IIa</i> and <i>IIb</i> treated with primary or secondary amines provided intermediates <i>IIIa-IIIc</i> which were hydrolyzed to N-acetonyl derivatives <i>IVa</i> and <i>IVb</i>, respectively. N-Benzylation of ethyl 7-chloro-6-fluoro-1,4-dihydro-4-oxoquinoline-3-carboxylate (<i>Va</i>) followed by hydrolysis yielded 1-benzyl-7-chloro-6-fluoro-1,4-dihydro-4-oxoquinoline-3-carboxylic acid (<i>Vd</i>) which upon a treatment with N-methylpiperazine provided <i>Ve</i>. Compound <i>Ve</i> was hydrogenated on Pd to 6-fluoro-1,4-dihydro-7-(4-methyl-1-piperazinyl)-4-oxoquinoline-3-carboxylic acid (<i>Vf</i>).

Title:Some reactions of N-propadienyl-4-quinolones
Creators:
Rádl, Stanislav
Kovářová, Lenka
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:56
Number:11
Page Range:pp. 2413-2419
ISSN:0010-0765
E-ISSN:1212-6950
Publisher:Institute of Organic Chemistry and Biochemistry
Related URLs:
URLURL Type
http://dx.doi.org/10.1135/cccc19912413UNSPECIFIED
ID Code:5172
Item Type:Article
Deposited On:22 Feb 2010 11:32
Last Modified:22 Feb 2010 10:32

Citation

Rádl, Stanislav; Kovářová, Lenka (1991) Some reactions of N-propadienyl-4-quinolones. Collection of Czechoslovak Chemical Communications, 56 (11). pp. 2413-2419. ISSN 0010-0765

Repository Staff Only: item control page