Pyridine-Imidazlolium Salts: Oxidatively Cleavage of N-C Bond via Nitration

Dumitrela Cucu (Diaconu),Violeta Mangalagiu

doi:10.3390/m1095

Abstract

Azaheterocycles derivatives with pyridine-imidazole skeleton are compounds of great value for medicinal chemistry. We report herein the nitration of 1,1′-(pyridine-2,6-diylbis(methylene))bis{3-[2-(4-nitrophenyl)-2-oxoethyl]-1H-imidazol-3-ium} bromide using a typical mixture of nitric and sulphuric acid. The nitration occur with the oxidative cleavage of N–C bond between imidazolium ring and methylene group.

Highlights

We perform the nitration of 1,10 -[pyridine-2,6-diylbis(methylene)]bis{3-[2-(4In this respect, we perform the nitration of nitrophenyl)-2-oxoethyl]-1H-imidazol-3-ium} bromide 1, using a typical mixture of nitric and sulphuric
Nitration of 1,10 -[pyridine-2,6-diylbis(methylene)]bis{3-[2-(4-nitrophenyl)-2oxoethyl]-1H-imidazol-3-ium} bromide occur with the oxidative cleavage of N–C bond between imidazolium ring and methylene group, with the formation of two side products 2,6-bis[(1Himidazol-1-yl)methyl]pyridine 2 and 4-nitrobenzoic acid 3
2,6-Bis[(1H-imidazol-1-yl)methyl]pyridine 2, was initially synthetized by Garrison and Co [22]; in the supporting information of the paper all the data concerning the compound can be found for comparison

Summary

Introduction

In and six six member member ring ring azaheterocycles azaheterocycles compounds, compounds, especially especially imidazole imidazole and (di)azine, became invaluable scaffolds in drug designing because of their large variety biological and (di)azine, became invaluable scaffolds in drug designing because of their largeofvariety of activities, such as anticancer, antimicrobial (antibacterial, antifungal, antitubercular), antimalarial, biological activities, such as anticancer, antimicrobial (antibacterial, antifungal, antitubercular), anti-inflammatory, antidepressant, analgesic, antihypertensive etc. [1–7]. In and six six member member ring ring azaheterocycles azaheterocycles compounds, compounds, especially especially imidazole imidazole and (di)azine, became invaluable scaffolds in drug designing because of their large variety biological and (di)azine, became invaluable scaffolds in drug designing because of their largeofvariety of activities, such as anticancer, antimicrobial (antibacterial, antifungal, antitubercular), antimalarial, biological activities, such as anticancer, antimicrobial (antibacterial, antifungal, antitubercular), anti-inflammatory, antidepressant, analgesic, antihypertensive etc. Taking into consideration our expertise in the area of obtaining new biologically active with antimicrobial activity [8–14]. Using cycloimmonium ylides chemistry [15–21], we decided to study compounds with antimicrobial activity [8–14] using cycloimmonium ylides chemistry [15–21], we the reactions of pyridine-imidazolium salts with nitric acid. Decided to study the reactions of pyridine-imidazolium salts with nitric acid

Results and Discussion

Instrumentation

Nitration of Pyridine-Imidazolium Salts