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

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

Journal

ARKIVOC
ISSN: 1551-7004 , E-ISSN: 1551-7012

Output data

Year: 2014, Pages: 132-144 Pages count : DOI: 10.3998/ark.5550190.p008.663

Tags

alpha-Ketoacetylenes; ethylenediamine; Michael addition; triple bond cleavage; arylmethylketones; 4,5-dihydro-1H-imidazoles

Authors

Vasilevsky Sergei F. ^1,2 , Davydova Maria P. ¹ , Tomilin Denis N. ³ , Sobenina Lyubov N. ³ , Mamatuyk Victor I. ^2,4 , Pleshkova Nadezhda V. ⁴

Affiliations

1	(Данные Web of science) Russian Acad Sci, Siberian Branch, VV Voevodsky Inst Chem Kinet & Combust, 3 Inst Skaya Str, Novosibirsk 630090, Russia
2	(Данные Web of science) Novosibirsk State Univ, Novosibirsk 630090, Russia
3	(Данные Web of science) Russian Acad Sci, AE Favorsky Irkutsk Inst Chem, Siberian Branch, Irkutsk 664033, Russia
4	(Данные Web of science) Russian Acad Sci, NN Vorozhtsov Novosibirsk Inst Organ Chem, Siberian Branch, Novosibirsk 630090, Russia

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 Michael-addition. 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.

Vasilevsky S.F. , Davydova M.P. , Tomilin D.N. , Sobenina L.N. , Mamatuyk V.I. , Pleshkova N.V.
Peculiarities of the cascade cleavage of the polarized C C-fragment in alpha-ketoacetylenes on reaction with ethylene diamine

ARKIVOC. 2014. P.132-144. DOI: 10.3998/ark.5550190.p008.663 WOS Scopus РИНЦ

Full text from publisher

Published online:

Jul 19, 2014

Web of science	WOS:000345779400008
Scopus	2-s2.0-84905497668
Elibrary	23978104
OpenAlex	W1998755221