Synthesis of novel imidazole‐4,5‐dicarboxylic acid derivatives

Yasuda, Naohiko

doi:10.1002/jhet.5570220239

Cited by 9 publications

(2 citation statements)

References 8 publications

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“…Synthesis. The synthesis of the symmetric I45DCs 1 − 8 , 17 , and 18 was done from the pyrazine diacid dichloride through modification of known procedures (Scheme ). ,, The I45DCs with smaller alkyl chains (methyl and propyl) retain significant water solubility that reduces the isolated yields as compared with the I45DCs substituted with the more hydrophobic amines. An improved method for the synthesis of the dissymmetric I45DCs 9 − 11 was recently reported .…”

Section: Resultsmentioning

confidence: 99%

Intramolecular Hydrogen Bonding and Intermolecular Dimerization in the Crystal Structures of Imidazole-4,5-dicarboxylic Acid Derivatives

Baures

Rush

Wiznycia

et al. 2002

Crystal Growth & Design

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Diamide and amide-ester derivatives of imidazole-4,5-dicarboxylic acid form reliable hydrogen-bonding motifs in the solid state. The crystal structures of symmetrically substituted and dissymmetrically substituted diamides as well as amide-ester combinations were analyzed in order to identify the intermolecular hydrogen-bonding patterns. An intramolecular seven-membered hydrogen-bonded conformation forms in all derivatives where the possibility existed due to the functionality present. The motifs observed for the diamides include intermolecular NH···O and NH···N hydrogen-bonded dimers, with the exceptions to these motifs occurring in compounds having benzylamine substituents. The amines with a higher classification (i.e., 3° > 2° > 1°) in the dissymmetrically substituted diamides are the intramolecular hydrogen bond donors in the solid state, consistent with the capacity of the alkyl group to stabilize developing carbocation character resulting from bond polarization. The amide-ester derivatives also form an intramolecular hydrogen bond and an intermolecular motif based on NH···N and two different C2−H···O hydrogen bonds. A pyrrole amide-ester derivative forms an intramolecular NH···O hydrogen bond in the solid state and an intermolecular NH···O hydrogen-bonded chain. With the exception of the benzylamine-substituted diamides, the intermolecular hydrogen-bonded motifs appear reliable for these imidazole-4,5-dicarboxylic acid derivatives and will be useful in the design of analogues for specific applications.

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Section: Resultsmentioning

confidence: 99%

Intramolecular Hydrogen Bonding and Intermolecular Dimerization in the Crystal Structures of Imidazole-4,5-dicarboxylic Acid Derivatives

Baures

Rush

Wiznycia

et al. 2002

Crystal Growth & Design

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“…Meldrum's and amino acids, Gopalsamy and Shi have synthesized similar carboxamides in a four step transformation [22]. Rather than adopt these two strategies, and in view of a recent report by Baures and co-workers [23], we turned our attention to a direct condensation of the amino acids with the appropriate imidazole-4(5)-(di)carboxylic acid derivatives [24][25].…”

Section: Introductionmentioning

confidence: 99%

Design and synthesis of optically active 2‐phenylimidazolecarboxamides featuring amino acid motive

Sívek

Pytela

Bureš

2008

Journal of Heterocyclic Chem

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Overall sixteen new, optically active carboxamides 1-3 have been synthesized. These compounds based on the 2-phenylimidazole and featuring amino acid residues are linked on the 4-position by an amidic bond. Two general methods were used for their construction. Whereas the first method employs acylchlorides as a reactive species, the second one involves a condensation of mixed anhydrides with the amino acid counterparts. Actually, the second method proved to be more efficient than the first one. Carboxamides 1-3 were preliminarily tested as N-chelating ligands with an application in the Henry or Aldol reactions affording either poor yields or enantiomeric excesses.

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ChemInform Abstract: SYNTHESIS OF NOVEL IMIDAZOLE‐4,5‐DICARBOXYLIC ACID DERIVATIVES

Yasuda¹

1985

Chemischer Informationsdienst

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Synthesis of novel imidazole‐4,5‐dicarboxylic acid derivatives

Cited by 9 publications

References 8 publications

Intramolecular Hydrogen Bonding and Intermolecular Dimerization in the Crystal Structures of Imidazole-4,5-dicarboxylic Acid Derivatives

Intramolecular Hydrogen Bonding and Intermolecular Dimerization in the Crystal Structures of Imidazole-4,5-dicarboxylic Acid Derivatives

Design and synthesis of optically active 2‐phenylimidazolecarboxamides featuring amino acid motive

ChemInform Abstract: SYNTHESIS OF NOVEL IMIDAZOLE‐4,5‐DICARBOXYLIC ACID DERIVATIVES

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