6533b831fe1ef96bd1299086

RESEARCH PRODUCT

5-Substituted 4,5-Dihydro-1,2,4-triazin-3(2H)-ones from the Unprecedented Reaction between α-N-Protected Amino Acid Hydrazides and NaBH4

Giancarlo VerardoPaola GeattiPaolo StrazzoliniMarcello Merli

subject

chemistry.chemical_classificationHydrazideCarbon atomAmino acids Cyclization- reduction reactions Heterocycles Hydrazides Sodium borohydrideHeterocycleOrganic ChemistryGeneral MedicineCyclization- reduction reactionsHeterocyclesHydrazidesHydrazideMedicinal chemistryAmino acidAmino acidchemistry.chemical_compoundSodium borohydridechemistryCyclization–reduction reactionsAmino acidsOrganic chemistryPhysical and Theoretical ChemistryRacemizationSodium borohydride

description

α-N-Protected amino acid hydrazides (1) readily reacted with NaBH4 to afford 5-substituted 4,5-dihydro-1,2,4-triazin-3(2H)-one derivatives 2 in good yields. Unfortunately, the reaction caused partial racemization at the α-amino acidic carbon atom of the starting hydrazide. A mechanism, supported by experimental evidence, has been proposed in an attempt to explain this to date unprecedented reaction. The structure of compounds 2 was confirmed by X-ray structural analysis. (© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2006)

yearjournalcountryeditionlanguage
2006-01-01European Journal of Organic Chemistry
https://doi.org/10.1002/ejoc.200500989