Synthesis of Boronated Amidines by Addition of Amines to Nitrilium Derivative of Cobalt Bis(Dicarbollide)

被引：9
作者：
Bogdanova, Ekaterina, V [1 ,2 ]
Stogniy, Marina Yu [1 ,2 ]
Suponitsky, Kyrill Yu [1 ,3 ]
Sivaev, Igor B. [1 ]
Bregadze, Vladimir, I [1 ]
机构：
[1] Russian Acad Sci, AN Nesmeyanov Inst Organoelement Cpds, 28 Vavilov St, Moscow 119991, Russia
[2] MIREA Russian Technol Univ, MV Lomonosov Inst Fine Chem Technol, 86 Vernadsky Av, Moscow 119571, Russia
[3] GV Plekhanov Russian Univ Econ, Basic Dept Chem Innovat Mat & Technol, 36 Stremyannyi Line, Moscow 117997, Russia
来源：
MOLECULES | 2021年 / 26卷 / 21期
基金：
俄罗斯科学基金会;
关键词：
cobalt bis(dicarbollide); nitrilium derivatives; amidines; nucleophilic addition reactions; synthesis; structure; QUINOLINE-ARYLAMIDINE HYBRIDS; SECONDARY ALIPHATIC-AMINES; CLOSO-DECABORATE CLUSTERS; RADICAL-CATION SALTS; X-RAY STRUCTURE; NUCLEOPHILIC-ADDITION; TRANSITION-METALS; ACETONITRILE; METALLACARBORANE; COMPLEXES;
D O I：
10.3390/molecules26216544
中图分类号：
Q5 [生物化学]; Q7 [分子生物学];
学科分类号：
071010 ; 081704 ;
摘要：
A series of novel cobalt bis(dicarbollide) based amidines were synthesized by the nucleophilic addition of primary and secondary amines to highly activated B-N+& EQUIV;C-R triple bond of the propionitrilium derivative [8-EtC & EQUIV;N-3,3 & PRIME;-Co(1,2-C2B9H10)(1 & PRIME;,2 & PRIME;-C2B9H11)]. The reactions with primary amines result in the formation of mixtures of E and Z isomers of amidines, whereas the reactions with secondary amines lead selectively to the E-isomers. The crystal molecular structures of E-[8-EtC(NMe2)=HN-3,3 & PRIME;-Co(1,2-C2B9H10)(1 & PRIME;,2 & PRIME;-C2B9H11)], E-[8-EtC(NEt2)=HN-3,3 & PRIME;-Co(1,2- C2B9H10)(1 & PRIME;,2 & PRIME;-C2B9H11)] and E-[8-EtC(NC5H10)=HN-3,3 & PRIME;-Co(1,2-C2B9H10)(1 & PRIME;,2 & PRIME;-C2B9H11)] were determined by single crystal X-ray diffraction.</p>
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页数：16
相关论文
共 104 条
[1]   Dramatic Acceleration of an Acyl Transfer-Initiated Cascade by Using Electron-Rich Amidine-Based Catalysts [J].
Ahlemeyer, Nicholas A. ;
Streff, Emma V. ;
Muthupandi, Pandi ;
Birman, Vladimir B. .
ORGANIC LETTERS, 2017, 19 (24) :6486-6489
[2]   Amidines: their synthesis, reactivity, and applications in heterocycle synthesis [J].
Aly, Ashraf A. ;
Braese, Stefan ;
Gomaa, Mohsen A. -M. .
ARKIVOC, 2018, :85-138
[3]  
[Anonymous], 2014, APEX2 and SAINT
[4]   Bis(dicarbollide) Complexes of Transition Metals as a Platform for Molecular Switches. Study of Complexation of 8,8′-Bis(methylsulfanyl) Derivatives of Cobalt and Iron Bis(dicarbollides) [J].
Anufriev, Sergey A. ;
Timofeev, Sergey, V ;
Anisimov, Alexei A. ;
Suponitsky, Kyrill Yu ;
Sivaev, Igor B. .
MOLECULES, 2020, 25 (23)
[5]   Methylsulfanyl-Stabilized Rotamers of Cobalt Bis(dicarbollide) [J].
Anufriev, Sergey A. ;
Erokhina, Svetlana A. ;
Suponitsky, Kyrill Yu. ;
Godovikov, Ivan A. ;
Filippov, Oleg A. ;
de Biani, Fabrizia Fabrizi ;
Corsini, Maddalena ;
Chizhov, Alexander O. ;
Sivaev, Igor B. .
EUROPEAN JOURNAL OF INORGANIC CHEMISTRY, 2017, (38-39) :4444-4451
[6]  
Armarego WLF, 2009, PURIFICATION OF LABORATORY CHEMICALS, 6TH EDITION, P1
[7]   Dihydrogen Bonds in Salts of Boron Cluster Anions [BnHn]2- with Protonated Heterocyclic Organic Bases [J].
Avdeeva, Varvara V. ;
Vologzhanina, Anna V. ;
Malinina, Elena A. ;
Kuznetsov, Nikolai T. .
CRYSTALS, 2019, 9 (07)
[8]   Reactions of the homoleptic acetonitrile complexes of palladium and platinum with diethylamine [J].
Bacchi, Alessia ;
Amico, Daniela Belli Dell' ;
Calderazzo, Fausto ;
Labella, Luca ;
Pelizzi, Giancarlo ;
Marchetti, Fabio ;
Samaritani, Simona .
INORGANICA CHIMICA ACTA, 2010, 363 (11) :2467-2473
[9]   A facile approach towards amidinophenylalanine derivatives as building blocks for the synthesis of non-natural peptides and peptidomimetics [J].
Behrouz, Somayeh ;
Kuehl, Nikos ;
Klein, Christian D. .
TETRAHEDRON LETTERS, 2021, 81
[10]   Addition reactions of primary and secondary aliphatic amines to the benzonitrile ligands in cis- and trans-[PtCl2(NCPh)2] complexes.: X-ray structure of the amidine complex trans-[PtCl2{Z-N(H)=C(NHBut)Ph}2] [J].
Belluco, U ;
Benetollo, F ;
Bertani, R ;
Bombieri, G ;
Michelin, RA ;
Mozzon, M ;
Tonon, O ;
Pombeiro, AJL ;
da Silva, FCG .
INORGANICA CHIMICA ACTA, 2002, 334 (334) :437-447
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