Efficient bromination of polyaniline base to poly(2-bromoaniline)-bromide salt and its application as a recyclable catalyst for the synthesis of 2-methyl-4-anilino-1,2,3,4-tetrahydroquinolines

被引:0
作者
Boddula, Rajender [1 ]
Srinivasan, Palaniappan [1 ]
机构
[1] Indian Inst Chem Technol, CSIR, Polymers & Funct Mat Div, Hyderabad 500007, Andhra Pradesh, India
关键词
Polyaniline salt; Reusable catalyst; Green chemistry; Tetrahydroquinoline; Stereoselectivity; STEREOSELECTIVE-SYNTHESIS; COMPOSITE; ACID; ELECTRODES; POLYMERS; ANILINE; WATER;
D O I
10.1016/j.catcom.2014.08.011
中图分类号
O64 [物理化学(理论化学)、化学物理学];
学科分类号
070304 ; 081704 ;
摘要
Efficient bromination of polyaniline base to poly(2-bromoaniline)-bromide is successfully carried out using bromodimethylsulfonium bromide. Poly(2-bromoaniline)-bromide salt was obtained in a dry amorphous nature, having high conductivity (2.5 S/cm) with agglomerated spherical morphology. Poly(2-bromoaniline)bromide salt was proved to be a novel, efficient, reusable, cheaper and eco-friendly polymer-based solid acid catalyst in the reaction between aromatic amines and N-vinyl lactam under solvent-free conditions to provide 2-methyl-4-anilino-1,2,3,4-tetrahydroquinolines. These 2,4-disubstituted tetrahydroquinolines were synthesized with trans selectivity. (C) 2014 Elsevier B.V. All rights reserved.
引用
收藏
页码:94 / 98
页数:5
相关论文
共 29 条
[1]  
Abdelkader R., 2013, RES J RECENT SCI, V2, P1
[2]   A three-component coupling protocol for the synthesis of substituted hexahydropyrrolo[3,2-c]quinolines [J].
Batey, RA ;
Simoncic, PD ;
Lin, D ;
Smyj, RP ;
Lough, AJ .
CHEMICAL COMMUNICATIONS, 1999, (07) :651-652
[3]   Progress in preparation, processing and applications of polyaniline [J].
Bhadra, Sambhu ;
Khastgir, Dipak ;
Singha, Nikhil K. ;
Lee, Joong Hee .
PROGRESS IN POLYMER SCIENCE, 2009, 34 (08) :783-810
[4]   Use of iodine doped polyaniline salt in the stereoselective synthesis of 2-methyl-4-substituted-1,2,3,4-tetrahydroquinoline derivatives [J].
Boddula, Rajender ;
Srinivasan, Palaniappan .
CATALYSIS COMMUNICATIONS, 2013, 30 :56-60
[5]   Performance of a polyaniline(DMcT)/carbon fiber composite as cathode for rechargeable lithium batteries [J].
Canobre, SC ;
Davoglio, RA ;
Biaggio, SR ;
Rocha, RC ;
Bocchi, N .
JOURNAL OF POWER SOURCES, 2006, 154 (01) :281-286
[6]   Polymerization of aniline through simultaneous chemical and electrochemical routes [J].
Eftekhari, Ali ;
Jafarkhani, Parvaneh .
POLYMER JOURNAL, 2006, 38 (07) :651-658
[7]   CONFIGURATION AND CONFORMATION OF SO-CALLED BIS(ALKYLIDENEARYLAMINES) [J].
FUNABASHI, M ;
IWAKAWA, M ;
YOSHIMURA, J .
BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN, 1969, 42 (10) :2885-+
[8]   VIBRATIONAL-SPECTRA AND STRUCTURE OF POLYANILINE [J].
FURUKAWA, Y ;
UEDA, F ;
HYODO, Y ;
HARADA, I ;
NAKAJIMA, T ;
KAWAGOE, T .
MACROMOLECULES, 1988, 21 (05) :1297-1305
[9]   Study of polyaniline doped with trifluoromethane sulfonic acid in gas-diffusion electrodes for proton-exchange membrane fuel cells [J].
Gharibi, H ;
Zhiani, M ;
Entezami, AA ;
Mirzaie, RA ;
Kheirmand, M ;
Kakaei, K .
JOURNAL OF POWER SOURCES, 2006, 155 (02) :138-144
[10]   Electrochemistry of conductive polymers. 34. Two-dimensional correlation analysis of real-time spectroelectrochemical data for aniline polymerization [J].
Hong, SY ;
Jung, YM ;
Kim, SB ;
Park, SM .
JOURNAL OF PHYSICAL CHEMISTRY B, 2005, 109 (09) :3844-3850