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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)