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

Verardo Giancarlo | Zendy; Geatti Paola | Zendy; Merli Marcello | Zendy; Strazzolini Paolo | Zendy

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

Author(s) -

Verardo Giancarlo,

Geatti Paola,

Merli Marcello,

Strazzolini Paolo

Publication year - 2006

Publication title -

european journal of organic chemistry

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 0.825

H-Index - 155

eISSN - 1099-0690

pISSN - 1434-193X

DOI - 10.1002/ejoc.200500989

Subject(s) - chemistry , racemization , hydrazide , carbon atom , amino acid , reaction mechanism , reaction conditions , medicinal chemistry , organic chemistry , combinatorial chemistry , stereochemistry , catalysis , biochemistry , alkyl

α‐ N ‐Protected amino acid hydrazides ( 1 ) readily reacted with NaBH 4 to afford 5‐substituted 4,5‐dihydro‐1,2,4‐triazin‐3(2 H )‐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)

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