Peculiarities of the cascade cleavage of the polarized C - C-fragment in α-ketoacetylenes on reaction with ethylene diamine — National Research Tomsk Polytechnic University

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

Keywords

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

ASJC Scopus subject areas

Organic Chemistry

Access to Document

10.3998/ark.5550190.p008.663

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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 › peer-review

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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",

author = "Vasilevsky, {Sergei F.} and Davydova, {Maria P.} and Tomilin, {Denis N.} and Sobenina, {Lyubov N.} and Mamatuyk, {Victor I.} and Pleshkova, {Nadezhda V.}",

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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

Y1 - 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

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KW - Triple bond cleavage

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