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 |
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Keywords
- 4,5-dihydro-1 h-imidazoles
- Arylmethylketones
- Ethylenediamine
- Michael addition
- Triple bond cleavage
- α-Ketoacetylenes
ASJC Scopus subject areas
- Organic Chemistry
Cite this
Peculiarities of the cascade cleavage of the polarized C - C-fragment in α-ketoacetylenes on reaction with ethylene diamine. / Vasilevsky, Sergei F.; Davydova, Maria P.; Tomilin, Denis N.; Sobenina, Lyubov N.; Mamatuyk, Victor I.; Pleshkova, Nadezhda V.
In: Arkivoc, Vol. 2014, No. 5, 19.07.2014, p. 132-144.Research output: Contribution to journal › Article
}
TY - JOUR
T1 - Peculiarities of the cascade cleavage of the polarized C - C-fragment in α-ketoacetylenes on reaction with ethylene diamine
AU - Vasilevsky, Sergei F.
AU - Davydova, Maria P.
AU - Tomilin, Denis N.
AU - Sobenina, Lyubov N.
AU - Mamatuyk, Victor I.
AU - Pleshkova, Nadezhda V.
PY - 2014/7/19
Y1 - 2014/7/19
N2 - 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.
AB - 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.
KW - 4,5-dihydro-1 h-imidazoles
KW - Arylmethylketones
KW - Ethylenediamine
KW - Michael addition
KW - Triple bond cleavage
KW - α-Ketoacetylenes
UR - http://www.scopus.com/inward/record.url?scp=84905497668&partnerID=8YFLogxK
UR - http://www.scopus.com/inward/citedby.url?scp=84905497668&partnerID=8YFLogxK
U2 - 10.3998/ark.5550190.p008.663
DO - 10.3998/ark.5550190.p008.663
M3 - Article
AN - SCOPUS:84905497668
VL - 2014
SP - 132
EP - 144
JO - Arkivoc
JF - Arkivoc
SN - 1424-6376
IS - 5
ER -