New Preparation of 2-N-Alkyl(aryl)amino-5-methyl-4H-1,3-thiazin-4-ones and 3,4-Dihydro-5-methyl-2,4-dioxo-2H-1,3-thiazine

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Title:New Preparation of 2-N-Alkyl(aryl)amino-5-methyl-4H-1,3-thiazin-4-ones and 3,4-Dihydro-5-methyl-2,4-dioxo-2H-1,3-thiazine
Creators:
Koščík, Dušan
Dzurilla, Milan
Kutschy, Peter
Journal or Publication Title:
Collection of Czechoslovak Chemical Communications, 58, 4, pp. 893-901

Abstract

Addition-cyclization reactions of 3-bromo- and 3-chloro-2-methylpropenoylisothiocyanates with primary and secondary amines and alcohols have been studied. The formed addition products, thioureas, underwent cyclization of heating with ethanolic KOH or in dimethylformamide in the presence of lithium hydride. This method represents a new approach to 2-dialkyl(aryl)amino-5-methyl-4<i>H</i>-1,3-thiazin-4-ones. Addition reactions with alcohols afforded 3,4-dihydro-5-methyl-2,4-dioxo-2<i>H</i>-1,3-thiazine as the sole product. The structure of the synthesized compounds was confirmed by <sup>1</sup>H NMR, <sup>13</sup>C NMR, IR and mass spectroscopy.

Title:New Preparation of 2-N-Alkyl(aryl)amino-5-methyl-4H-1,3-thiazin-4-ones and 3,4-Dihydro-5-methyl-2,4-dioxo-2H-1,3-thiazine
Creators:
Koščík, Dušan
Dzurilla, Milan
Kutschy, Peter
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:58
Number:4
Page Range:pp. 893-901
ISSN:0010-0765
E-ISSN:1212-6950
Publisher:Institute of Organic Chemistry and Biochemistry
Related URLs:
URLURL Type
http://dx.doi.org/10.1135/cccc19930893UNSPECIFIED
ID Code:206
Item Type:Article
Deposited On:06 Feb 2009 16:59
Last Modified:06 Feb 2009 15:59

Citation

Koščík, Dušan; Dzurilla, Milan; Kutschy, Peter (1993) New Preparation of 2-N-Alkyl(aryl)amino-5-methyl-4H-1,3-thiazin-4-ones and 3,4-Dihydro-5-methyl-2,4-dioxo-2H-1,3-thiazine. Collection of Czechoslovak Chemical Communications, 58 (4). pp. 893-901. ISSN 0010-0765

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