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

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1 Citation (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)
Original languageEnglish
Pages (from-to)2638-2643
Number of pages6
JournalEuropean Journal of Organic Chemistry
Publication statusPublished - 2006

All Science Journal Classification (ASJC) codes

  • Physical and Theoretical Chemistry
  • Organic Chemistry

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