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 language | English |
|---|---|
| Pages (from-to) | 132-144 |
| Number of pages | 13 |
| Journal | Arkivoc |
| Volume | 2014 |
| Issue number | 5 |
| DOIs | |
| Publication status | Published - 19 Jul 2014 |
| Externally published | Yes |
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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Vasilevsky, S. F., Davydova, M. P., Tomilin, D. N., Sobenina, L. N., Mamatuyk, V. I., & Pleshkova, N. V. (2014). Peculiarities of the cascade cleavage of the polarized C - C-fragment in α-ketoacetylenes on reaction with ethylene diamine. Arkivoc, 2014(5), 132-144. https://doi.org/10.3998/ark.5550190.p008.663