Synthesis of unsymmetrical sulfides catalyzed by n-tetrabutyl-ammonium tribromide: A selective fluorescence probe for mercury ion

被引:9
作者
Dar, Ajaz A. [1 ]
Ali, Shahzad [1 ]
Ghosh, Arindam [1 ]
Khan, Abu T. [1 ,2 ]
Dwivedi, Atul K. [1 ]
Iyer, Parameswar K. [1 ]
机构
[1] Indian Inst Technol Guwahati, Dept Chem, Gauhati 781039, Assam, India
[2] Aliah Univ, Kolkata 700091, W Bengal, India
关键词
2-Naphthoquinone-1-methide; 2-Naphthol; Aromatic aldehydes; Thiols; n-tetrabutylammonium tribromide(TBATB) and Hg(II) sensor; O-QUINONE METHIDES; EFFICIENT CHEMOSELECTIVE REAGENT; ENVIRONMENTALLY BENIGN SYNTHESIS; CARBONYL-COMPOUNDS; CROSS-LINKING; TURN-ON; GENERATION; CONVENIENT; SENSOR; WATER;
D O I
10.1016/j.snb.2013.11.099
中图分类号
O65 [分析化学];
学科分类号
070302 ; 081704 ;
摘要
A wide variety of unsymmetrical sulfides can be synthesized by trapping 2-naphthoquinone-1-methide intermediates, which are generated in situ from 2-naphthol and aromatic aldehydes, with thiols in presence of catalytic amount of n-tetrabutylammonium tribromide (TBATB). Mild reaction conditions, good yields and no dithioacetal formation as well as formation of brominated product are some of the salient features of the present protocol. Interestingly, the synthesized unsymmetrical sulfide 4aa can be used as selective fluorescence probe for mercury(II) ion. (C) 2013 Elsevier B. V. All rights reserved.
引用
收藏
页码:509 / 514
页数:6
相关论文
共 46 条
[21]   New three-component condensation reaction: synthesis of 1-[(alkylthio)(phenyl)methyl]-naphthalene-2-ol catalyzed by bromodimethylsulfonium bromide (BDMS) [J].
Khan, Abu T. ;
Ali, Shahzad ;
Dar, Ajaz A. ;
Lal, Mohan .
TETRAHEDRON LETTERS, 2011, 52 (40) :5157-5160
[22]   Tetrabutylammonium tribromide (TBATB): a mild and efficient catalyst for O-isopropylidenation of carbohydrates [J].
Khan, Abu T. ;
Khan, Md Musawwer ;
Adhikary, Anubendu .
CARBOHYDRATE RESEARCH, 2011, 346 (05) :673-677
[23]   An Efficient and Convenient Approach for the Synthesis of Novel 2-Hydroxy-12-aryl-8,9,10,12-tetrahydrobenzo[a]xanthene-11-ones Using p-Toluenesulfonic acid in Ethanol and Ionic Liquid [J].
Khurana, Jitender M. ;
Nand, Bhaskara ;
Sneha .
JOURNAL OF HETEROCYCLIC CHEMISTRY, 2011, 48 (06) :1388-1392
[24]   Turn-On Fluorescent Sensor for Selective Detection of Zn2+, Cd2+, and Hg2+ in Water [J].
Li, Meng ;
Lu, Hai-Yan ;
Liu, Rui-Li ;
Chen, Jun-Dao ;
Chen, Chuan-Feng .
JOURNAL OF ORGANIC CHEMISTRY, 2012, 77 (07) :3670-3673
[25]   Efficient Generation of ortho-Quinone Methide: Application to the Biomimetic Syntheses of (±)-Schefflone and Tocopherol Trimers [J].
Liao, Daohong ;
Li, Houhua ;
Lei, Xiaoguang .
ORGANIC LETTERS, 2012, 14 (01) :18-21
[26]   Mild and efficient synthesis of bis-indolylmethanes catalyzed by tetrabutylammonium tribromide [J].
Lin, Xu-Feng ;
Cui, Sun-Liang ;
Wang, Yan-Guang .
SYNTHETIC COMMUNICATIONS, 2006, 36 (21) :3153-3160
[27]   The real-time detection of trace-level Hg2+ in water by QCM loaded with thiol-functionalized SBA-15 [J].
Lou, Huihui ;
Zhang, Yuan ;
Xiang, Qun ;
Xu, Jiagiang ;
Li, Hui ;
Xu, Pengcheng ;
Li, Xinxin .
SENSORS AND ACTUATORS B-CHEMICAL, 2012, 166 :246-252
[28]  
Marsini M.A., 2008, ORGANIC LETT, V10, P1477
[29]   Trapping a Labile Adduct Formed between an ortho-Quinone Methide and 2′-Deoxycytidine [J].
McCrane, Michael P. ;
Weinert, Emily E. ;
Lin, Ying ;
Mazzola, Eugene P. ;
Lam, Yiu-Fai ;
Scholl, Peter F. ;
Rokita, Steven E. .
ORGANIC LETTERS, 2011, 13 (05) :1186-1189
[30]   A useful and convenient synthetic protocol for interconversion of carbonyl compounds to the corresponding 1,3-oxathiolanes and vice versa employing organic ammonium tribromide (OATB) [J].
Mondal, E ;
Sahu, PR ;
Bode, G ;
Khan, AT .
TETRAHEDRON LETTERS, 2002, 43 (15) :2843-2846