Study of the reaction between carbamoyl azides of α-N-protected amino acids and hydrazine monohydrate

Giancarlo Verardo, Cesare Daniele Venneri, Gennaro Esposito, Paolo Strazzolini

Research output: Contribution to journalArticle

Abstract

Two simple and efficient synthetic methods for the preparation of semicarbazide amino acid derivatives are reported. The procedures involve reaction between the carbamoyl azides of α-N-protected amino acids and hydrazine monohydrate: 4-[(alkoxycarbonylamino)(alkyl)methyl]semicarbazides 1 are obtained when hydrazine is added to the separated tetrahydrofuran (THF) solution containing the carbamoyl azide at 0 °C, whereas 1-[(alkoxycarbonylamino)(alkyl)methyl-carbamoyl]-4-[(alkoxycarbonylamino)(alkyl) methyl]semicarbazides 4 are produced by adding hydrazine directly into the final THF/aqueous buffer (KH2PO4) biphasic mixture containing the prepared carbamoyl azide at 50 °C, respectively. NMR experimental data obtained from samples dissolved in [D6]dimethyl sulfoxide suggest a dimeric association for semicarbazides 4 with intermolecular hydrogen bonds. Moreover, the ESI-MS-MS spectra reveal some interesting common features.

Original languageEnglish (US)
Pages (from-to)1376-1384
Number of pages9
JournalEuropean Journal of Organic Chemistry
Issue number7
DOIs
StatePublished - Mar 1 2011

Fingerprint

hydrazine
Semicarbazides
Azides
hydrazines
amino acids
tetrahydrofuran
Amino Acids
Dimethyl Sulfoxide
Hydrogen bonds
Buffers
buffers
Nuclear magnetic resonance
Association reactions
hydrogen bonds
Derivatives
preparation
nuclear magnetic resonance

Keywords

  • Amino acids
  • Azides
  • Semicarbazides

ASJC Scopus subject areas

  • Organic Chemistry
  • Physical and Theoretical Chemistry

Cite this

Study of the reaction between carbamoyl azides of α-N-protected amino acids and hydrazine monohydrate. / Verardo, Giancarlo; Venneri, Cesare Daniele; Esposito, Gennaro; Strazzolini, Paolo.

In: European Journal of Organic Chemistry, No. 7, 01.03.2011, p. 1376-1384.

Research output: Contribution to journalArticle

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