4,5-Dihydroimidazoles from Dithiocarboxylic Esters, Thiocarboxamides, or Nitriles

Lévesque, Guy; Gressier, J.C.; PROUST, M.

doi:10.1055/s-1981-29659

Cited by 50 publications

(9 citation statements)

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“…Chemistry N-aryl-2-amino-3-cyanopyrroles 1a-d were obtained by reaction of a-hydroxy ketones (namely; benzoin or phenacyl bromide) with different aryl amine and malonodinitrile according to a procedure defined in the literature 50,64,65 . Reaction of nitriles, carboxylic acids, esters, ortho-esters or hydroxyamides with ethylenediamine, using carbon disulphide as solvent, is a well-known method for preparation of the corresponding 2-substituted imidazolines, as used here for the preparation of compounds 3-(2-dihydroimidazolyl)pyrrole-2-amines 2a-d [66][67][68][69] . The structures of these compounds were confirmed by spectral analysis; IR spectra showed disappearance of CN absorption bands and appearance of absorption frequency for NH at 3403-3290 cm À1 .…”

Section: Resultsmentioning

confidence: 99%

Synthesis of novel pyrroles and fused pyrroles as antifungal and antibacterial agents

El-Hameed

Sayed

Ali

et al. 2021

Journal of Enzyme Inhibition and Medicinal Chemistry

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Pyrroles and its fused forms possess antimicrobial activities, they can easily interact with biomolecules of living systems. A series of substituted pyrroles, and its fused pyrimidines and triazines forms have been synthesised, all newly synthesised compound structures were confirmed by spectroscopic analysis. Generally, the compounds inhibited growth of some important human pathogens, the best effect was given by: 2a, 3c, 4d on Gram-positive bacteria and was higher on yeast ( C. albican s), by 5c on Gram-negative bacteria and by 5a then 3c on filamentous fungi (A. fumigatus and F. oxysporum ). Such results present good antibacterial and antifungal potential candidates to help overcome the global problem of antibiotic resistance and opportunistic infections outbreak. Compound 3c gave the best anti-phytopathogenic effect at a 50-fold lower concentration than Kocide 2000, introducing a safe commercial candidate for agricultural use. The effect of the compounds on DNA was monitored to detect the mode of action.

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Section: Resultsmentioning

confidence: 99%

Synthesis of novel pyrroles and fused pyrroles as antifungal and antibacterial agents

El-Hameed

Sayed

Ali

et al. 2021

Journal of Enzyme Inhibition and Medicinal Chemistry

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“…In 1981, Levesque et al reported the condensation of dithioesters with diamines under mild conditions. [30] Chlorodicyanovinylbenzene 18 can be considered as an equivalent of benzoyl chloride. [31] One molar equivalent of malonitrile and HCl was extruded during the condensation through a retro-Knoevenagel reaction and addition-elimination.…”

Section: Synthesis Of 2-imidazolines From 12-diamines (Methods A)mentioning

confidence: 99%

Recent Advances in the Synthesis of 2‐Imidazolines and Their Applications in Homogeneous Catalysis

Liu

2009

Adv Synth Catal

143

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As an important class of heterocyclic scaffolds, 2‐imidazolines have attracted the attention from the chemists interested in natural products, pharmaceutical chemistry, synthetic organic chemistry, coordination chemistry, and homogeneous catalysis. To fulfill the demand of structural diversity, many efficient methods towards 2‐imidazolines, as well as modifications of traditional methods, have been reported in the past two decades. 2‐Imidazolines have been developed as ligands in homogeneous catalysis, for the substitution on the nitrogen atom that provides an opportunity for fine‐tuning of the electronic effect. This review summarizes recent advances in the synthesis of 2‐imidazolines and their applications in homogeneous catalysis.

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“…1,3,5-Trisubstituted pyrazolines 1 were synthesized according to the reported procedure [13]. 2-Substituted imidazolines 3 were synthesized according to the reported procedure [21,22]. .…”

Section: Methodsmentioning

confidence: 99%

Metal-free oxidative dehydrogenation of imidazolines and pyrazolines using silica-adsorbed peroxymonosulfate under aprotic and almost neutral conditions

Adibi

Hajipour

Jafari

2008

Chem Heterocycl Comp

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4,5-Dihydroimidazoles from Dithiocarboxylic Esters, Thiocarboxamides, or Nitriles

Cited by 50 publications

References 0 publications

Synthesis of novel pyrroles and fused pyrroles as antifungal and antibacterial agents

Synthesis of novel pyrroles and fused pyrroles as antifungal and antibacterial agents

Recent Advances in the Synthesis of 2‐Imidazolines and Their Applications in Homogeneous Catalysis

Metal-free oxidative dehydrogenation of imidazolines and pyrazolines using silica-adsorbed peroxymonosulfate under aprotic and almost neutral conditions

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