Synthesis of 3-Substituted 3-Dihydro-1-1phenylamino-1H-pyrrolo[1,2-a]imidazole-2,5(3H,6H)-diones from alfa-Amino Acid Phenylhydrazides and Levulinic Acid. (Articolo in rivista)

Type
Label
  • Synthesis of 3-Substituted 3-Dihydro-1-1phenylamino-1H-pyrrolo[1,2-a]imidazole-2,5(3H,6H)-diones from alfa-Amino Acid Phenylhydrazides and Levulinic Acid. (Articolo in rivista) (literal)
Anno
  • 2004-01-01T00:00:00+01:00 (literal)
Alternative label
  • Verardo G., Geatti P., Merli M., Castellarin E. (2004)
    Synthesis of 3-Substituted 3-Dihydro-1-1phenylamino-1H-pyrrolo[1,2-a]imidazole-2,5(3H,6H)-diones from alfa-Amino Acid Phenylhydrazides and Levulinic Acid.
    in European journal of organic chemistry (Print)
    (literal)
Http://www.cnr.it/ontology/cnr/pubblicazioni.owl#autori
  • Verardo G., Geatti P., Merli M., Castellarin E. (literal)
Pagina inizio
  • 2833 (literal)
Pagina fine
  • 2839 (literal)
Rivista
Note
  • ISI Web of Science (WOS) (literal)
Titolo
  • Synthesis of 3-Substituted 3-Dihydro-1-1phenylamino-1H-pyrrolo[1,2-a]imidazole-2,5(3H,6H)-diones from alfa-Amino Acid Phenylhydrazides and Levulinic Acid. (literal)
Abstract
  • Alfa-Amino acid phenylhydrazides 1 readily react with levulinic acid to produce the imidazolidin-4-one intermediates 4, which undergo a second ring closure to afford the dihydro-1H-pyrrolo[1,2-a]imidazole-2,5-dione derivatives 5. It has been established that the solvent polarity has a great influence on the rate of the second condensation reaction, but not on the first. A mechanism, supported by experimental evidence, has been proposed to explain how the imidazolidin-4-one intermediates 4, obtained as expected as a mixture of two diastereoisomers, give a single isomer for the bicyclic derivatives 5; the absolute stereochemistry of these compounds has been determined by X-ray crystallographic analysis. (literal)
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