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.

VERARDO, G, GEATTI, P, MARTINUZZI, M, et al. (2004). SYNTHESIS OF 3-SUBSTITUTED DIHYDRO-1-1PHENYLAMINO-1H-PYRROLO[1,2-A]IMIDAZOLE-2,5(3H,6H)-DIONES FROM A-AMINO ACID PHENYLHYDRAZIDES AND LEVULINIC ACID. EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2004, 2833-2839 [10.1002/ejoc.200500989].

SYNTHESIS OF 3-SUBSTITUTED DIHYDRO-1-1PHENYLAMINO-1H-PYRROLO[1,2-A]IMIDAZOLE-2,5(3H,6H)-DIONES FROM A-AMINO ACID PHENYLHYDRAZIDES AND LEVULINIC ACID

MERLI, Marcello
2004-01-01

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.
2004
VERARDO, G, GEATTI, P, MARTINUZZI, M, et al. (2004). SYNTHESIS OF 3-SUBSTITUTED DIHYDRO-1-1PHENYLAMINO-1H-PYRROLO[1,2-A]IMIDAZOLE-2,5(3H,6H)-DIONES FROM A-AMINO ACID PHENYLHYDRAZIDES AND LEVULINIC ACID. EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2004, 2833-2839 [10.1002/ejoc.200500989].
File in questo prodotto:
Non ci sono file associati a questo prodotto.

I documenti in IRIS sono protetti da copyright e tutti i diritti sono riservati, salvo diversa indicazione.

Utilizza questo identificativo per citare o creare un link a questo documento: https://hdl.handle.net/10447/18980
Citazioni
  • ???jsp.display-item.citation.pmc??? ND
  • Scopus 1
  • ???jsp.display-item.citation.isi??? 1
social impact