9-isothiocyanatoanthracene as a versatile starting compound in the chemistry of anthracen-9-yl derivatives

被引:11
作者
Janovec, L
Suchár, G
Imrich, J
Kristian, P [1 ]
Sasinková, V
Alföldi, J
Sedlák, E
机构
[1] Safarik Univ, Dept Organ Chem, SK-04167 Kosice, Slovakia
[2] Slovak Acad Sci, Inst Chem, SK-84238 Bratislava, Slovakia
[3] Safarik Univ, Fac Sci, Dept Biochem, SK-04167 Kosice, Slovakia
关键词
isothiocyanates; thioureas; 9-isothiocyanatoanthracene; anthracenylthioureas; kinetics; IR spectroscopy; C-13 NMR spectroscopy; fluorescence;
D O I
10.1135/cccc20020665
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
The synthesis, structure and reactivity of 9-isothiocyanatoanthracene (5) likewise the conformation of the corresponding thioureas (6a-6i) have been studied. The C-13 NMR substituent chemical shift values of the NCS group and correlations between spectral parameters (IR, NMR) and rate constans of reactions of 5, acridin-9-yl (14), phenyl (15) and benzoyl isothiocyanate (16) with butylamine were found. Significant increase of the fluorescence of the synthesized anthracenylthioureas with amino acid rests refers to the possibility to use 5 as potential biomarker.
引用
收藏
页码:665 / 678
页数:14
相关论文
共 33 条
[1]   C-13 NMR-SPECTRA AND SUBSTITUENT EFFECTS OF META-SUBSTITUTED AND PARA-SUBSTITUTED BENZOYL ISOTHIOCYANATES [J].
DANIHEL, I ;
IMRICH, J ;
KOSCIK, D ;
KRISTIAN, P ;
BARANCIKOVA, G .
COLLECTION OF CZECHOSLOVAK CHEMICAL COMMUNICATIONS, 1985, 50 (06) :1422-1431
[2]  
DANIHEL I, 1984, CHEM ZVESTI, V38, P539
[3]   AN ANALYSIS OF SUBSTITUENT EFFECTS ON THE PROTON AND C-13 CHEMICAL-SHIFTS OF 2-SUBSTITUTED 9-ISOTHIOCYANATOACRIDINES [J].
DANIHEL, I ;
IMRICH, J ;
KRISTIAN, P ;
LIPTAJ, T ;
MAZAGOVA, D .
COLLECTION OF CZECHOSLOVAK CHEMICAL COMMUNICATIONS, 1994, 59 (08) :1833-1840
[4]  
Drobinca L., 1977, CHEM CYANATES THEIR, P1003
[5]  
FAURE R, 1980, CHEM SCRIPTA, V15, P62
[6]   Meso aldehydes of anthracene and 1,2-benzanthracene [J].
Fieser, LF ;
Hartwell, JL .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1938, 60 :2555-2559
[7]   Reactions of organic thiosulphates. [J].
Footner, HB ;
Smiles, S .
JOURNAL OF THE CHEMICAL SOCIETY, 1925, 127 :2887-2891
[8]   1,3-DIPOLAR CYCLOADDITION OF CARBON DISULFIDE TO A NITRILE OXIDE [J].
FOYE, WO ;
KAUFFMAN, JM .
JOURNAL OF ORGANIC CHEMISTRY, 1966, 31 (07) :2417-&
[9]   NITRILE OXIDES .6. SOME NOVEL ADDITION REACTIONS OF AROMATIC NITRILE OXIDES [J].
GRUNDMAN.C ;
FROMMELD, HD .
JOURNAL OF ORGANIC CHEMISTRY, 1966, 31 (01) :157-&
[10]   NITRILE OXIDES .V. STABLE AROMATIC NITRILE OXIDES [J].
GRUNDMANN, C ;
DEAN, JM .
JOURNAL OF ORGANIC CHEMISTRY, 1965, 30 (08) :2809-+