Construction of bis-, tris- and tetrahydrazones by addition of azoalkenes to amines and ammonia

Exhaustive Michael-type alkylations of amines and ammonia with azoalkenes (generated from α-halohydrazones) were demonstrated as an efficient approach to poly(hydrazonomethyl)amines – a novel class of polynitrogen ligands. An intramolecular cyclotrimerization of C=N bonds in tris(hydrazonomethyl)ami...

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Main Authors:	Artem N. Semakin, Aleksandr O. Kokuev, Yulia V. Nelyubina, Alexey Yu. Sukhorukov, Petr A. Zhmurov, Sema L. Ioffe, Vladimir A. Tartakovsky
Format:	Article
Language:	English
Published:	Beilstein-Institut 2016-11-01
Series:	Beilstein Journal of Organic Chemistry
Subjects:	azoalkenes α-halogen hydrazones heterocage compounds hydrazone ligands Michael addition
Online Access:	https://doi.org/10.3762/bjoc.12.241

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spelling	doaj-06c80b8b0f8045d1a9535c841deeafd52021-02-02T08:46:46ZengBeilstein-InstitutBeilstein Journal of Organic Chemistry1860-53972016-11-011212471247710.3762/bjoc.12.2411860-5397-12-241Construction of bis-, tris- and tetrahydrazones by addition of azoalkenes to amines and ammoniaArtem N. Semakin0Aleksandr O. Kokuev1Yulia V. Nelyubina2Alexey Yu. Sukhorukov3Petr A. Zhmurov4Sema L. Ioffe5Vladimir A. Tartakovsky6Laboratory of functional organic compounds, N.D. Zelinsky Institute of Organic Chemistry Russian Academy of Sciences, Leninsky Prospect, 47, Moscow, 119991, RussiaMoscow Chemical Lyceum 1303, Tamozhenniy proezd, 4, Moscow, 111033, RussiaLaboratory for X-Ray Diffraction Studies, A.N.Nesmeyanov Institute of Organoelement Compounds of Russian Academy of Sciences, Vavilova Str. 28, Moscow, 119991, RussiaLaboratory of functional organic compounds, N.D. Zelinsky Institute of Organic Chemistry Russian Academy of Sciences, Leninsky Prospect, 47, Moscow, 119991, RussiaLaboratory of functional organic compounds, N.D. Zelinsky Institute of Organic Chemistry Russian Academy of Sciences, Leninsky Prospect, 47, Moscow, 119991, RussiaLaboratory of functional organic compounds, N.D. Zelinsky Institute of Organic Chemistry Russian Academy of Sciences, Leninsky Prospect, 47, Moscow, 119991, RussiaLaboratory of functional organic compounds, N.D. Zelinsky Institute of Organic Chemistry Russian Academy of Sciences, Leninsky Prospect, 47, Moscow, 119991, RussiaExhaustive Michael-type alkylations of amines and ammonia with azoalkenes (generated from α-halohydrazones) were demonstrated as an efficient approach to poly(hydrazonomethyl)amines – a novel class of polynitrogen ligands. An intramolecular cyclotrimerization of C=N bonds in tris(hydrazonomethyl)amine to the respective 1,4,6,10-tetraazaadamantane derivative was demonstrated.https://doi.org/10.3762/bjoc.12.241azoalkenesα-halogen hydrazonesheterocage compoundshydrazone ligandsMichael addition
collection	DOAJ
language	English
format	Article
sources	DOAJ
author	Artem N. Semakin Aleksandr O. Kokuev Yulia V. Nelyubina Alexey Yu. Sukhorukov Petr A. Zhmurov Sema L. Ioffe Vladimir A. Tartakovsky
spellingShingle	Artem N. Semakin Aleksandr O. Kokuev Yulia V. Nelyubina Alexey Yu. Sukhorukov Petr A. Zhmurov Sema L. Ioffe Vladimir A. Tartakovsky Construction of bis-, tris- and tetrahydrazones by addition of azoalkenes to amines and ammonia Beilstein Journal of Organic Chemistry azoalkenes α-halogen hydrazones heterocage compounds hydrazone ligands Michael addition
author_facet	Artem N. Semakin Aleksandr O. Kokuev Yulia V. Nelyubina Alexey Yu. Sukhorukov Petr A. Zhmurov Sema L. Ioffe Vladimir A. Tartakovsky
author_sort	Artem N. Semakin
title	Construction of bis-, tris- and tetrahydrazones by addition of azoalkenes to amines and ammonia
title_short	Construction of bis-, tris- and tetrahydrazones by addition of azoalkenes to amines and ammonia
title_full	Construction of bis-, tris- and tetrahydrazones by addition of azoalkenes to amines and ammonia
title_fullStr	Construction of bis-, tris- and tetrahydrazones by addition of azoalkenes to amines and ammonia
title_full_unstemmed	Construction of bis-, tris- and tetrahydrazones by addition of azoalkenes to amines and ammonia
title_sort	construction of bis-, tris- and tetrahydrazones by addition of azoalkenes to amines and ammonia
publisher	Beilstein-Institut
series	Beilstein Journal of Organic Chemistry
issn	1860-5397
publishDate	2016-11-01
description	Exhaustive Michael-type alkylations of amines and ammonia with azoalkenes (generated from α-halohydrazones) were demonstrated as an efficient approach to poly(hydrazonomethyl)amines – a novel class of polynitrogen ligands. An intramolecular cyclotrimerization of C=N bonds in tris(hydrazonomethyl)amine to the respective 1,4,6,10-tetraazaadamantane derivative was demonstrated.
topic	azoalkenes α-halogen hydrazones heterocage compounds hydrazone ligands Michael addition
url	https://doi.org/10.3762/bjoc.12.241
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Construction of bis-, tris- and tetrahydrazones by addition of azoalkenes to amines and ammonia

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