Facile cyclization of 2-arylethynyl aniline to 4(1H)-cinnolones: a new chemodosimeter for nitrite ions

被引:19
作者
Dey, Raju [1 ]
Chatterjee, Tanmay [1 ]
Ranu, Brindaban C. [1 ]
机构
[1] Indian Assoc Cultivat Sci, Dept Organ Chem, Kolkata 700032, India
关键词
Cinnolone; Chemodosimeter; Detection of nitrite ion; Arylethynyl aniline; COLORIMETRIC NITRITE; NITRATE; CINNOLINES;
D O I
10.1016/j.tetlet.2010.11.098
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
2-Arylethynyl anilines undergo very fast reaction (5 min) with nitrite ions in aqueous acidic media to produce 4(1H)-cinnolones which exhibit yellow color and UV absorbance at 391 nm. This reaction is irreversible and has been successfully tested for the detection of nitrite ions in water at ppm concentration. Thus, 2-phenylethynyl aniline serves as a chemodosimeter. An efficient and general method for the synthesis of 4(1H)-cinnolones has been developed based on this reaction. (C) 2010 Elsevier Ltd. All rights reserved.
引用
收藏
页码:461 / 464
页数:4
相关论文
共 25 条
[1]   Green chemistry tools to influence a medicinal chemistry and research chemistry based organisation [J].
Alfonsi, Kim ;
Colberg, Juan ;
Dunn, Peter J. ;
Fevig, Thomas ;
Jennings, Sandra ;
Johnson, Timothy A. ;
Kleine, H. Peter ;
Knight, Craig ;
Nagy, Mark A. ;
Perry, David A. ;
Stefaniak, Mark .
GREEN CHEMISTRY, 2008, 10 (01) :31-36
[2]   Efficient sensing of nitrite by Fe(bpy)32+ immobilized Nafion modified electrodes [J].
Azad, Uday Pratap ;
Ganesan, Vellaichamy .
CHEMICAL COMMUNICATIONS, 2010, 46 (33) :6156-6158
[3]   Nitrite- and chloride-selective fluorescent nano-optodes and in in vitro application to rat conceptuses [J].
Barker, SLR ;
Thorsrud, BA ;
Kopelman, R .
ANALYTICAL CHEMISTRY, 1998, 70 (01) :100-104
[4]   Facile Cyclization of Terphenyl to Triphenylene: A New Chemodosimeter for Fluoride Ions [J].
Bhalla, Vandana ;
Singh, Hardev ;
Kumar, Manoj .
ORGANIC LETTERS, 2010, 12 (03) :628-631
[5]   Palladium catalyzed alkynylation of aryl halides (Sonogashira reaction) in water [J].
Bhattacharya, S ;
Sengupta, S .
TETRAHEDRON LETTERS, 2004, 45 (47) :8733-8736
[6]   Solid-phase synthesis of substituted cinnolines by a Richter type cleavage protocol [J].
Bräse, S ;
Dahmen, S ;
Heuts, J .
TETRAHEDRON LETTERS, 1999, 40 (34) :6201-6203
[7]   Determination of nitrite in waters by microplate fluorescence spectroscopy and HPLC with fluorescence detection [J].
Büldt, A ;
Karst, U .
ANALYTICAL CHEMISTRY, 1999, 71 (15) :3003-3007
[9]   Colorimetric Nitrite and Nitrate Detection with Gold Nanoparticle Probes and Kinetic End Points [J].
Daniel, Weston L. ;
Han, Min Su ;
Lee, Jae-Seung ;
Mirkin, Chad A. .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2009, 131 (18) :6362-+
[10]  
Doyel J. M., 2000, LIEBIGS ANN CHEM, V72, P2302