Synthesis of Alkyl- and Phenyl-2-thiouracils and 1,3-Thiazin-4-ones by Nucleophilic Substitution of Unsymmetrical Thioureas with 3-Chloropropenoates

[img]PDF - Authorized users only
Language: English
94Kb
Title:Synthesis of Alkyl- and Phenyl-2-thiouracils and 1,3-Thiazin-4-ones by Nucleophilic Substitution of Unsymmetrical Thioureas with 3-Chloropropenoates
Creators:
Jalander, Lars F.
Lönnqvist, Jan-Erik
Journal or Publication Title:
Collection of Czechoslovak Chemical Communications, 64, 8, pp. 1307-1315
Uncontrolled Keywords:2-Thiouracils, 1,3-Thiazin-4-ones, Pyrimidines, Thioureas, Nucleophilic substitutions, Cyclization

Abstract

Unsymmetrically substituted thioureas and ethyl (<i>E</i>)- and (<i>Z</i>)-3-aryl-3-chloro-2-cyano- propenoates (<strong>1a</strong>) and (<strong>1b</strong>) gave after nucleophilic vinylic substitution and cyclisation two isomers of 1,3-disubstituted 6-aryl-5-cyano-2-thiouracil derivatives, <strong>3a</strong>-<strong>3i</strong> and <strong>4a</strong>-<strong>4i</strong>. Substituted 1,3-thiazin-4-ones <strong>5a</strong>-<strong>5d</strong> were formed in moderate to good yields when monosubstituted thioureas were allowed to react under similar conditions. <p>

Title:Synthesis of Alkyl- and Phenyl-2-thiouracils and 1,3-Thiazin-4-ones by Nucleophilic Substitution of Unsymmetrical Thioureas with 3-Chloropropenoates
Creators:
Jalander, Lars F.
Lönnqvist, Jan-Erik
Uncontrolled Keywords:2-Thiouracils, 1,3-Thiazin-4-ones, Pyrimidines, Thioureas, Nucleophilic substitutions, 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:8
Page Range:pp. 1307-1315
ISSN:0010-0765
E-ISSN:1212-6950
Publisher:Institute of Organic Chemistry and Biochemistry
Related URLs:
URLURL Type
http://dx.doi.org/10.1135/cccc19991307UNSPECIFIED
ID Code:1557
Item Type:Article
Deposited On:06 Feb 2009 17:10
Last Modified:06 Feb 2009 16:10

Citation

Jalander, Lars F.; Lönnqvist, Jan-Erik (1999) Synthesis of Alkyl- and Phenyl-2-thiouracils and 1,3-Thiazin-4-ones by Nucleophilic Substitution of Unsymmetrical Thioureas with 3-Chloropropenoates. Collection of Czechoslovak Chemical Communications, 64 (8). pp. 1307-1315. ISSN 0010-0765

Repository Staff Only: item control page