Peculiarities of the cascade cleavage of the polarized C - C-fragment in α-ketoacetylenes on reaction with ethylene diamine

Sergei F. Vasilevsky, Maria P. Davydova, Denis N. Tomilin, Lyubov N. Sobenina, Victor I. Mamatuyk, Nadezhda V. Pleshkova

Research output: Contribution to journalArticle

2 Citations (Scopus)

Abstract

The reaction of diarylketoacetylenes with ethylenediamine (EDA) leads to arylmethylketones and 2-substituted imidazoline derivatives. This transformation involves complete cleavage of the triple bond via initial intermolecular Michael-addition with subsequent intramolecular Michaeladdition. Final fragmentation can be presented as a retro-Mannich reaction, accompanied by three formal reductive stages (formation of three C-H bonds), while the other carbon undergoes a formal oxidation, in which three C-N bonds (C-N and C=N) are formed.

Original languageEnglish
Pages (from-to)132-144
Number of pages13
JournalArkivoc
Volume2014
Issue number5
DOIs
Publication statusPublished - 19 Jul 2014
Externally publishedYes

Keywords

  • 4,5-dihydro-1 h-imidazoles
  • Arylmethylketones
  • Ethylenediamine
  • Michael addition
  • Triple bond cleavage
  • α-Ketoacetylenes

ASJC Scopus subject areas

  • Organic Chemistry

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