A Simple and Practical Synthesis of 2-Aminoimidazoles

Little, Thomas L.; Webber, S. E.

doi:10.1021/jo00103a021

Cited by 128 publications

(93 citation statements)

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“…The microanalyses were performed on a Perkin-Elmer 240C elemental analyzer. The compounds 4-aryloxazol-2-amine 43) (1), 4-arylthiazol-2-amine 43) (2), 4-aryl-1H-imidazol-2-amine 44) (3) and Z-(arylethenesulfonyl) acetic acid 45) required as the starting materials were prepared by adopting the literature precedent.…”

Section: Methodsmentioning

confidence: 99%

“…Chemistry For the synthesis of bis heterocycles mentioned in the scheme, the compounds 4-aryloxazol-2-amine 43) (1), 4-arylthiazol-2-amine 43) (2), 4-aryl-1H-imidazol-2-amine 44) (3) and Z-(arylethenesulfonyl) acetic acid 45) required as the starting materials were prepared by adopting the literature precedent. The Z-(arylethenesulfonyl) acetyl chloride (4) was prepared by the chlorination of Z-(arylethenesulfonyl) acetic acid with thionyl chloride.…”

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confidence: 99%

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Synthesis and Antimicrobial Activity of Azole Derivatives

Prakash

Reddy

Padmaja

et al. 2013

CHEMICAL & PHARMACEUTICAL BULLETIN

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A new class of mono and bis heterocycles, sulfonylmethaneamido linked oxazoles, thiazoles, imidazoles, pyrrolyl oxazoles, pyrrolyl thiazoles and pyrrolyl imidazoles were prepared adopting simple and versatile synthetic methodologies. The compound chloro substituted imidazolyl styrylsulfonylacetamide is the most potent antimicrobial agent particularly against Pseudomonas aeruginosa and Penicillium chrysogenum.

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Section: Methodsmentioning

confidence: 99%

mentioning

confidence: 99%

Synthesis and Antimicrobial Activity of Azole Derivatives

Prakash

Reddy

Padmaja

et al. 2013

CHEMICAL & PHARMACEUTICAL BULLETIN

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“…Several synthetic methods have been reported in the literature to obtain 2-aminoimidazoles that involve the construction of the heterocycle, 1 including the addition of substituted guanidines 12,13 or 2-aminopyrimidines (protected guanidines) 14 to α-haloketones, the basemediated semi cleavage of hemiaminals obtained by reaction of N-Boc protected guanidines and N-carbomethoxy-1,2-dihydropyridines, 15 or the condensation of cyanamide and α-aminoketones 16 or α-aminoesters. 6 In a similar way, the corresponding 2-aminoimidazolines have been synthesized by condensation of N-arylcarbonimidodithioates and ethylenediamine, 17,18 and by intramolecular cyclization of functionalized arylthioureas, obtained by reaction of isothiocyanatobenzene and ethylenediamine.…”

Section: Figurementioning

confidence: 99%

C-N bond forming reactions in the synthesis of substituted 2-aminoimidazole derivatives

Gómez-SanJuan¹,

Botija²,

Méndez³

et al. 2013

Arkivoc

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Carbon-nitrogen bond forming reactions oriented to the synthesis of 2-amino-imidazolidines and imidazoles have been investigated. The C-2 amination of imidazolidinones, via the corresponding 2-chlorodihydroimidazoles, led to 2-benzylaminodihydroimidazole or bis(dihydroimidazole)amino derivatives by choosing the adequate experimental conditions. On the other hand, the use of N-acyl-2-methylsulfanyldihydroimidazoles allowed carrying out the reactions with aromatic amines, such as p-anisidine. Finally, palladium catalyzed BuchwaldHartwig amination was the method of choice for C-N coupling between 2-haloimidazoles and aromatic amines in the synthesis of the corresponding imidazoles.

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“…A variation of the Hantzsch synthesis has been introduced for the preparation of 2-aminoimidazoles using a-haloketones and N-acetylguanidines to afford the corresponding 4(5)-substituted N-(1H-imidazol-2-yl)acetamides 298. These compounds are then hydrolyzed to their corresponding 2-aminoimidazoles 299 (Scheme 10.171) [475].…”

Section: 56mentioning

confidence: 99%