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Synthesis of new Bis-imidazole derivatives


Jasinski, M; Mloston, G; Mucha, P; Linden, A; Heimgartner, H (2007). Synthesis of new Bis-imidazole derivatives. Helvetica Chimica Acta, 90(9):1765-1780.

Abstract

The reaction of aldimines with alpha-(hydroxyimino) ketones of type 10 (1,2-diketone monooximes) was used to prepare 2-unsubstituted imidazole 3-oxides 11 bearing an alkanol chain at N(1) (Scheme 2, Table 1). These products were transformed into the corresponding 2H-imidazol-2-ones 13 and 2H-imidazole-2-thiones 14 by treatment with Ac2O and 2,2,4,4-tetramethylcyclobutane-1,3-dithione, respectively (Scheme 3). The three-component reaction of 10, formaldehyde, and an alkane-1,omega-diamine
15 gave the bis[1H-imidazole 3-oxides] 16 (Scheme 4, Table 2). With Ac2O, 2,2,4,4-tetramethylcyclobutane-1,3-dithione or Raney-Ni, the latter reacted to give the corresponding bis[2H-imidazol-2-ones] 19 and 20, bis[2H-imidazol-2-thione] 21, and bis[imidazole] 22, respectively (Schemes 5 and 6).
The structures of 11a and 16b were established by X-ray crystallography.

Abstract

The reaction of aldimines with alpha-(hydroxyimino) ketones of type 10 (1,2-diketone monooximes) was used to prepare 2-unsubstituted imidazole 3-oxides 11 bearing an alkanol chain at N(1) (Scheme 2, Table 1). These products were transformed into the corresponding 2H-imidazol-2-ones 13 and 2H-imidazole-2-thiones 14 by treatment with Ac2O and 2,2,4,4-tetramethylcyclobutane-1,3-dithione, respectively (Scheme 3). The three-component reaction of 10, formaldehyde, and an alkane-1,omega-diamine
15 gave the bis[1H-imidazole 3-oxides] 16 (Scheme 4, Table 2). With Ac2O, 2,2,4,4-tetramethylcyclobutane-1,3-dithione or Raney-Ni, the latter reacted to give the corresponding bis[2H-imidazol-2-ones] 19 and 20, bis[2H-imidazol-2-thione] 21, and bis[imidazole] 22, respectively (Schemes 5 and 6).
The structures of 11a and 16b were established by X-ray crystallography.

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Additional indexing

Item Type:Journal Article, refereed, original work
Communities & Collections:07 Faculty of Science > Department of Chemistry
Dewey Decimal Classification:540 Chemistry
Language:English
Date:2007
Deposited On:07 Nov 2011 13:52
Last Modified:18 Apr 2018 11:41
Publisher:Verlag Helvetica Chimica Acta
ISSN:0018-019X
Funders:Ministry of Science and Higher Education, Poland, F. Hoffmann-La Roche AG, Basel
OA Status:Green
Publisher DOI:https://doi.org/10.1002/hlca.200790186

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