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 journal › Article

1 Citation (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 language	English
Pages (from-to)	132-144
Number of pages	13
Journal	Arkivoc
Volume	2014
Issue number	5
DOIs	https://doi.org/10.3998/ark.5550190.p008.663
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

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

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

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.",

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

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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

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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

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KW - Ethylenediamine

KW - Michael addition

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10.3998/ark.5550190.p008.663