Synthesis of 2-aminobenzothiazole via FeCl3-catalyzed tandem reaction of 2-iodoaniline with isothiocyanate in water

被引:96
作者
Ding, Qiuping [1 ,2 ]
Cao, Banpeng [1 ]
Liu, Xianjin [1 ]
Zong, Zhenzhen [1 ]
Peng, Yi-Yuan [2 ]
机构
[1] Jiangxi Normal Univ, Coll Chem & Chem Engn, Nanchang 330022, Peoples R China
[2] Key Lab Green Chem Jiangxi Prov, Nanchang 330022, Peoples R China
基金
中国国家自然科学基金;
关键词
SUPERCRITICAL CARBON-DIOXIDE; CATALYZED INTRAMOLECULAR CYCLIZATION; FLUOROUS MEDIA; ROUTE; TRANSFORMATIONS; EFFICIENT; 2-ALKYNYLBENZALDOXIME; BENZOTHIAZOLES; STRATEGY; SOLVENT;
D O I
10.1039/c0gc00123f
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
An FeCl3-catalyzed tandem reaction of 2-iodoaniline with isothiocyanate in water is described, which provides an environmentally benign, efficient, and practical route for the generation of 2-aminobenzothiazole. This present tandem process shows broad substrate scope in the presence of octadecyltrimethylammonium chloride as a phase-transfer catalyst. In addition, the reaction media can be recovered and recycled without loss of efficiency.
引用
收藏
页码:1607 / 1610
页数:4
相关论文
共 54 条
[1]   Conversion of the laboratory synthetic route of the N-aryl-2-benzothiazolamine R116010 to a manufacturing method [J].
Aelterman, W ;
Lang, Y ;
Willemsens, B ;
Vervest, I ;
Leurs, S ;
De Knaep, F .
ORGANIC PROCESS RESEARCH & DEVELOPMENT, 2001, 5 (05) :467-471
[2]   Copper-catalyzed tandem conjugate addition-electrophilic trapping: Ketones, esters, and nitriles as terminal electrophiles [J].
Agapiou, K ;
Cauble, DF ;
Krische, MJ .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2004, 126 (14) :4528-4529
[3]   Synthesis of 2-substituted-benzothiazoles by palladium-catalyzed intramolecular cyclization of o-bromophenylthioureas and o-bromophenylthioamides [J].
Benedí, C ;
Bravo, F ;
Uriz, P ;
Fernández, E ;
Claver, C ;
Castillón, S .
TETRAHEDRON LETTERS, 2003, 44 (32) :6073-6077
[4]   Synthesis of (+)-CP-263,114 [J].
Chen, C ;
Layton, ME ;
Sheehan, SM ;
Shair, MD .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2000, 122 (30) :7424-7425
[5]  
Chen SL, 2007, ACS SYM SER, V950, P161
[6]   Ionic transformations in extremely nonpolar fluorous media: Phase transfer catalysis of halide substitution reactions [J].
Consorti, Crestina S. ;
Jurisch, Markus ;
Gladysz, John A. .
ORGANIC LETTERS, 2007, 9 (12) :2309-2312
[7]   Fluorous methods for synthesis and separation of organic molecules [J].
Curran, DP .
PURE AND APPLIED CHEMISTRY, 2000, 72 (09) :1649-1653
[8]   Tandem [4+2]/[3+2] cycloadditions of nitroalkenes [J].
Denmark, SE ;
Thorarensen, A .
CHEMICAL REVIEWS, 1996, 96 (01) :137-165
[9]   Access to functionalized isoquinoline N-oxides via sequential electrophilic cyclization/cross-coupling reactions [J].
Ding, Qiuping ;
Wu, Jie .
ADVANCED SYNTHESIS & CATALYSIS, 2008, 350 (11-12) :1850-1854
[10]   A facile route to 2,4-dihydro-1H-benzo[d][1,3]thiazines via silver-catalyzed tandem addition-cyclization reactions [J].
Ding, Qiuping ;
Wu, Jie .
JOURNAL OF COMBINATORIAL CHEMISTRY, 2008, 10 (04) :541-545