Synthesis and Characterization of Some New 4-Methyl-5-Imidazole Carbaldehyde Derivatives

Year 2019, Volume: 6 Issue: 3, 373 - 382, 20.10.2019

Ersin Orhan Mahmut Köse Demet Alkan Leyla Öztürk

https://doi.org/10.18596/jotcsa.530757

Abstract

Imidazole is a common and important heterocyclic
fragment of many biologically important molecules. 5-imidazole-carbaldehydes
containing mono- (N-1) methyl (or aryl) analogs are commonly used as building
blocks in medical chemistry. In this study, starting from
4-methyl-1H-imidazole-5-carbaldehyde, the N-1 atom of the imidazole ring is
derived with different alkyl groups. In addition, both N atoms of the starting
imidazole-carbaldehyde were methylated to give
5-carbaldehyde-1,3,4-trimethyl-3-imidazolium salt. The salt which possess quite
reactive carbaldehyde group could be used as a precursor for synthesis of other
imidazolium derivatives. Furthermore, 4-methyl-5-imidazole carbaldehyde was
converted into the benzoxazole, benzothiazole and benzoimidazole by a two-step
reaction over the aldehyde group. These new compounds could display some
biological activities.

Keywords

Imidazole, imidazolium derivatives

Supporting Institution

Bülent Ecevit University and Düzce University

Project Number

Bülent Ecevit University Grant no: BAP 2014-72118496-06) and Düzce University Grant No.: 2012.05.03.097

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