Synthesis and selected transformations of 3-oxido-1H-imidazole-4-carboxamides

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Title:Synthesis and selected transformations of 3-oxido-1H-imidazole-4-carboxamides
Creators:
Mloston, Grzegorz
Jasiński, Marcin
Journal or Publication Title:
Collection of Czechoslovak Chemical Communications, 75, 8, pp. 871-885
Uncontrolled Keywords:1,3-Dipolar cycloaddition, Carboxamides, Direct arylation, Imidazole <i>N</i>-oxides, Hydrogen bond

Abstract

An efficient synthesis of new <i>N</i>-alkyl- and <i>N</i>-aryl-3-oxido-1<i>H</i>-imidazole-4-carboxamides based on exploration of inexpensive, commercially available ethyl acetoacetate, paraformaldehyde and primary amines is described. Representative compounds were tested in selected transformations, such as ‘sulfur-transfer reaction’ leading to imidazole-2-thiones and isomerization to corresponding imidazol-2-ones. Strong intramolecular hydrogen bonding via the <i>N</i>-oxide function results in the reduced reactivity of 3-oxido-1<i>H</i>-imidazole-4-carboxamides in both reactions. Moreover, the palladium catalyzed C(2)-arylation of imidazole ring as well as azide-alkyne [3+2] cycloaddition using the <i>N</i>-propargyl substituted 4-carboxamide derived from an imidazole 3-oxide as a dipolarophile, were also studied.

Title:Synthesis and selected transformations of 3-oxido-1H-imidazole-4-carboxamides
Creators:
Mloston, Grzegorz
Jasiński, Marcin
Uncontrolled Keywords:1,3-Dipolar cycloaddition, Carboxamides, Direct arylation, Imidazole <i>N</i>-oxides, Hydrogen bond
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:75
Number:8
Page Range:pp. 871-885
E-ISSN:1212-6950
Publisher:Institute of Organic Chemistry and Biochemistry
Related URLs:
URLURL Type
http://dx.doi.org/10.1135/cccc2010012UNSPECIFIED
ID Code:6196
Item Type:Article
Deposited On:11 Oct 2010 15:42
Last Modified:11 Oct 2010 13:43

Citation

Mloston, Grzegorz; Jasiński, Marcin (2010) Synthesis and selected transformations of 3-oxido-1H-imidazole-4-carboxamides. Collection of Czechoslovak Chemical Communications, 75 (8). pp. 871-885.

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