Synthesis of 2-Ureido-4-ferrocenyl Pyrimidine Guests. Investigation of Complementary Molecular Recognition of 2,6-Diaminopyridine

被引:8
作者
Feher, Csaba [1 ]
Papp, Mate [1 ]
Gomory, Agnes [2 ,4 ]
Nagy, Livia
Wouters, Johan [5 ]
Lendvay, Gyorgy [3 ,6 ]
Skoda-Foldes, Rita [1 ]
机构
[1] Univ Pannonia, Inst Chem, Dept Organ Chem, Egyet U 10,POB 158, H-8200 Veszprem, Hungary
[2] Hungarian Acad Sci, Instrumentat Ctr, H-1117 Budapest, Hungary
[3] Hungarian Acad Sci, Inst Mat & Environm Chem, Res Ctr Nat Sci, H-1117 Budapest, Hungary
[4] Univ Pecs, Janos Szentagothai Res Ctr, Ifjusag Utja 20, H-7624 Pecs, Hungary
[5] Univ Namur, Dept Chem, B-5000 Namur, Belgium
[6] Univ Pannonia, Inst Chem, Dept Gen & Inorgan Chem, H-8200 Veszprem, Hungary
关键词
ASYMMETRIC-SYNTHESIS; FERROCENE; DERIVATIVES; UREAS;
D O I
10.1021/acs.organomet.6b00586
中图分类号
O61 [无机化学];
学科分类号
070301 ; 081704 ;
摘要
Novel 2-ureido-4-ferrocenylpyrimidines have been synthesized from iodoferrocene by a three-step reaction sequence. XRD analysis and spectroscopic data support the presence of an intramolecular hydrogen, bond between a nitrogen, atom of the pyrimidine ring and an NH group of the urea moiety. Both theoretical calculations and NMR investigations prove the existence of two isomeric forms in solution, both of which can form hydrogen bonds with an appropriate guest via an acceptor donor acceptor bonding pattern. Complexation with 2,6-diaminopyridine can be proved either by NMR spectroscopy or by electrochemical measurements.
引用
收藏
页码:4023 / 4032
页数:10
相关论文
共 32 条
[1]   Probing the solvent-induced tautomerism of a redox-active ureidopyrimidinone [J].
Alexander, Anne-Marie ;
Bria, Marc ;
Brunklaus, Gunther ;
Caldwell, Stuart ;
Cooke, Graeme ;
Garety, James F. ;
Hewage, Shanika G. ;
Hocquel, Yann ;
McDonald, Niall ;
Rabani, Gouher ;
Rosair, Georgina ;
Smith, Brian O. ;
Spiess, Hans Wolfgang ;
Rotello, Vincent M. ;
Woisel, Patrice .
CHEMICAL COMMUNICATIONS, 2007, (22) :2246-2248
[2]   Effective recognition of H2PO4- by a new series of dendrimers functionalized with ferrocenyl-urea termini [J].
Alonso, B ;
Casado, CM ;
Cuadrado, I ;
Morán, M ;
Kaifer, AE .
CHEMICAL COMMUNICATIONS, 2002, (16) :1778-1779
[3]  
[Anonymous], PLATON MULTIPURPOSE
[4]   Strong dimerization of ureidopyrimidones via quadruple hydrogen bonding [J].
Beijer, FH ;
Sijbesma, RP ;
Kooijman, H ;
Spek, AL ;
Meijer, EW .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1998, 120 (27) :6761-6769
[5]   Mediated biosensors [J].
Chaubey, A ;
Malhotra, BD .
BIOSENSORS & BIOELECTRONICS, 2002, 17 (6-7) :441-456
[6]   Ferrocene incorporating host-guest dyads with electrochemically controlled three-pole hydrogen bonding properties [J].
Cooke, G ;
de Cremiers, HA ;
Duclairoir, FMA ;
Leonardi, J ;
Rosair, G ;
Rotello, VM .
TETRAHEDRON, 2003, 59 (18) :3341-3347
[7]   Synthesis of ferrocene-labelled 2-aminopyrimidine derivatives via homogeneous catalytic carbonylation [J].
Feher, Csaba ;
Habus, Ivan ;
Wouters, Johan ;
Skoda-Foeldes, Rita .
MONATSHEFTE FUR CHEMIE, 2014, 145 (12) :1981-1986
[8]   A two-step synthesis of ferrocenyl pyrazole and pyrimidine derivatives based on carbonylative Sonogashira coupling of iodoferrocene [J].
Feher, Csaba ;
Kuik, Arpad ;
Mark, Laszlo ;
Kollar, Laszlo ;
Skoda-Foeldes, Rita .
JOURNAL OF ORGANOMETALLIC CHEMISTRY, 2009, 694 (25) :4036-4041
[9]   Photoinduced Triplet-Triplet Energy Transfer in a 2-Ureido-4(1H)-Pyrimidinone-Bridged, Quadruply Hydrogen-Bonded Ferrocene-Fullerene Assembly [J].
Feng, Ke ;
Yu, Mao-Lin ;
Wang, Su-Min ;
Wang, Ge-Xia ;
Tung, Chen-Ho ;
Wu, Li-Zhu .
CHEMPHYSCHEM, 2013, 14 (01) :198-203
[10]  
Frisch M.J., 2016, Gaussian, V16