Effect of cyclodextrins on coupling of o-ethoxybenzenediazonium salt with pyrrole, imidazole and 2-methylimidazole

被引:2
作者
Jamrogiewicz, Marzena [1 ]
Sadowska, Kamila [1 ]
Biernat, Jan F. [1 ]
机构
[1] Gdansk Univ Technol, PL-80952 Gdansk, Poland
关键词
cyclodextrins; diazonium salts; coupling reactions; pyrrole; imidazole; 2-methylimidazole;
D O I
10.1007/s10847-006-9115-0
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
The effect of beta-cyclodextrin on o-ethoxybenzenediazonium salt coupling with pyrrole, imidazole and 2-methylimidazole has been studied. The differences in the reaction course, the overall yield and products distribution have been analyzed. Experiments without cyclodextrins and selected reactions with alpha- and gamma-cyclodextrins have been performed for comparison. The results are discussed in terms of co-conformation of azole molecules embedded in cyclodextrin cavity.
引用
收藏
页码:355 / 362
页数:8
相关论文
共 41 条
[31]  
SZEJTLI J, 1988, CYCLOEXTRIN TECHNOLO, P366
[32]   Organic reactions mediated by cyclodextrins [J].
Takahashi, K .
CHEMICAL REVIEWS, 1998, 98 (05) :2013-2033
[33]   Recent aspects of pharmaceutical application of cyclodextrins [J].
Uekama, K .
JOURNAL OF INCLUSION PHENOMENA AND MACROCYCLIC CHEMISTRY, 2002, 44 (1-4) :3-7
[34]   A MODIFIED CYCLODEXTRIN AS A GUEST RESPONSIVE COLOR-CHANGE INDICATOR [J].
UENO, A ;
KUWABARA, T ;
NAKAMURA, A ;
TODA, F .
NATURE, 1992, 356 (6365) :136-137
[35]   Chromogenic macrocyclic derivatives of azoles-synthesis and properties [J].
Wagner-Wysiecka, E ;
Luboch, E ;
Kowalczyk, M ;
Biernat, JF .
TETRAHEDRON, 2003, 59 (24) :4415-4420
[36]   Chromoionophores with chromophores as integral part(s) of the macrocycle in crown ethers [J].
Wagner-Wysiecka, E ;
Luboch, E ;
Biernat, JF .
JOURNAL OF INCLUSION PHENOMENA AND MACROCYCLIC CHEMISTRY, 2001, 41 (1-4) :19-22
[37]   ELECTROPHILIC CATALYSIS BY CYCLODEXTRINS [J].
YE, HP ;
RONG, D ;
DSOUZA, VT .
TETRAHEDRON LETTERS, 1991, 32 (39) :5231-5234
[38]   DYNAMIC ASPECTS IN HOST-GUEST INTERACTIONS .4. KINETIC AND H-1-NMR EVIDENCE FOR MULTISTEP DIRECTIONAL BINDING IN THE MOLECULAR RECOGNITION OF SOME 2-NAPHTHYLAZOPHENOL GUESTS WITH ALPHA-CYCLODEXTRIN [J].
YOSHIDA, N .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 2, 1995, (12) :2249-2256
[39]   DYNAMIC ASPECTS IN HOST-GUEST INTERACTIONS .2. DIRECTIONAL INCLUSION REACTIONS OF SOME AZO GUEST MOLECULES WITH ALPHA-CYCLODEXTRIN [J].
YOSHIDA, N ;
HAYASHI, K .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 2, 1994, (06) :1285-1290
[40]  
Zhang XY, 2000, ANGEW CHEM INT EDIT, V39, P544, DOI 10.1002/(SICI)1521-3773(20000204)39:3<544::AID-ANIE544>3.0.CO