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)
Data di pubblicazione: | giu-2006 |
Titolo: | 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 |
Autori: | Verardo, G; Geatti, P; Merli, M; Strazzolini, P |
Autori: | |
Tipologia: | Articolo su rivista |
Citazione: | Verardo, G., Geatti, P., Merli, M., & Strazzolini, P. (2006). 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. EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2006(11), 2638-2643. |
Tipo: | Articolo in rivista |
Appare nelle tipologie: | 01 - Articolo su rivista |
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