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

Marcello Merli; Paola Geatti; Paolo Strazzolini; Giancarlo Verardo

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

Marcello Merli, Paola Geatti, Paolo Strazzolini, Giancarlo Verardo

Scienze della Terra e del Mare

Risultato della ricerca: Article

1 Citazioni (Scopus)

Abstract

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)

Lingua originale	English
pagine (da-a)	2638-2643
Numero di pagine	6
Rivista	European Journal of Organic Chemistry
Stato di pubblicazione	Published - 2006

All Science Journal Classification (ASJC) codes

Physical and Theoretical Chemistry
Organic Chemistry

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title = "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",

abstract = "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. ({\textcopyright} Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2006)",

author = "Marcello Merli and Paola Geatti and Paolo Strazzolini and Giancarlo Verardo",

year = "2006",

language = "English",

pages = "2638--2643",

journal = "Annalen der Pharmacie",

issn = "0075-4617",

publisher = "Wiley-VCH Verlag",

}

TY - JOUR

T1 - 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

AU - Merli, Marcello

AU - Geatti, Paola

AU - Strazzolini, Paolo

AU - Verardo, Giancarlo

PY - 2006

Y1 - 2006

N2 - 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)

AB - 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)

UR - http://hdl.handle.net/10447/63265

M3 - Article

SP - 2638

EP - 2643

JO - Annalen der Pharmacie

JF - Annalen der Pharmacie

SN - 0075-4617

ER -