α-Azido ketones, part 8

Base-induced coupling of α-Azido ketones with a 1,2-diaza-1,3-diene as a Michael acceptor 1

Éva Juhász-Tóth, Gianfranco Favi, Orazio A. Attanasi, A. Bényei, T. Patonay

Research output: Contribution to journalArticle

2 Citations (Scopus)

Abstract

Carbanions generated from various acyclic and cyclic α-azido ketones in the presence of bases were reacted with ethyl 3-[(carbamoylimino)amino]but-2- enoate as a Michael acceptor to give the corresponding adducts. The adducts of acyclic azides were unstable and eliminated hydrazoic acid to give the corresponding ethyl 2-[1-[(carbamoylamino)imino]ethyl]-4-oxo-4-phenylbut-2- enoates as (E,E/Z,E)-diastereomeric mixtures. The relative configuration of these diastereomers was determined by X-ray analysis. Adducts of cyclic α-azido ketones were obtained in diastereomerically pure form, with the exception of 2-azidobenzosuberone.

Original languageEnglish
Article numberst-2014-d0332-l
Pages (from-to)2001-2004
Number of pages4
JournalSynlett
Volume25
Issue number14
DOIs
Publication statusPublished - 2014

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Ketones
Azides
X ray analysis
hydrazoic acid

Keywords

  • azides
  • carbanions
  • diazadienes
  • ketones
  • Michael additions

ASJC Scopus subject areas

  • Organic Chemistry

Cite this

α-Azido ketones, part 8 : Base-induced coupling of α-Azido ketones with a 1,2-diaza-1,3-diene as a Michael acceptor 1. / Juhász-Tóth, Éva; Favi, Gianfranco; Attanasi, Orazio A.; Bényei, A.; Patonay, T.

In: Synlett, Vol. 25, No. 14, st-2014-d0332-l, 2014, p. 2001-2004.

Research output: Contribution to journalArticle

Juhász-Tóth, Éva ; Favi, Gianfranco ; Attanasi, Orazio A. ; Bényei, A. ; Patonay, T. / α-Azido ketones, part 8 : Base-induced coupling of α-Azido ketones with a 1,2-diaza-1,3-diene as a Michael acceptor 1. In: Synlett. 2014 ; Vol. 25, No. 14. pp. 2001-2004.
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AU - Bényei, A.

AU - Patonay, T.

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