GREEN AND EFFICIENT METHOD FOR THIOCYANATION OF AROMATIC AND HETEROAROMATIC COMPOUNDS USING CROSS-LINKED POLY (4-VINYLPYRIDINE) SUPPORTED THIOCYANATE ION AS VERSATILE REAGENT AND OXONE AS MILD OXIDANT

被引：10
作者：
Ali, Mohammad [1 ]
Zarchi, Karimi [1 ]
Banihashemi, R. [1 ]
机构：
[1] Yazd Univ, Coll Sci, Dept Chem, Yazd, Iran
来源：
PHOSPHORUS SULFUR AND SILICON AND THE RELATED ELEMENTS | 2014年 / 189卷 / 09期
关键词：
Thiocyanation; oxone; regioselectivity; polymeric reagent; aryl thiocyanate; ARYL THIOCYANATES; REGIOSELECTIVE THIOCYANATION; DIAZOTIZATION-AZIDATION; NONAQUEOUS CONDITIONS; AMMONIUM THIOCYANATE; POLYMERIC REAGENT; SECONDARY-AMINES; FACILE SYNTHESIS; BORONIC ACIDS; ALKYL-HALIDES;
D O I：
10.1080/10426507.2013.865123
中图分类号：
O61 [无机化学];
学科分类号：
070301 ; 081704 ;
摘要：
A green and efficient regioselective thiocyanation of indoles, anilines and pyrrole has been achieved via a simple protocol using cross-linked poly (4-vinylpyridine) supported thiocyanate ion, [P-4-VP]SCN, as a versatile polymeric reagent and oxone as an environmentally friendly and mild oxidant. Various indoles, anilines, pyrroles, and carbazoles were transformed into their corresponding aryl thiocyanates in high to excellent yields in a short reaction time. The present procedure offers advantages such as simple reaction work-up, and the polymeric reagents can also be regenerated and reused several times without significant loss of their activity.
引用
收藏
页码：1378 / 1390
页数：13
相关论文
共 65 条
[1]   EFFICIENT AND NOVEL METHOD FOR THIOCYANATION OF AROMATIC COMPOUNDS USING TRICHLOROISOCYANURIC ACID/AMMONIUM THIOCYANATE/WET SiO2 [J].
Akhlaghinia, Batool ;
Pourali, Ali-Reza ;
Rahmani, Marzieh .
SYNTHETIC COMMUNICATIONS, 2012, 42 (08) :1184-1191
[2]  
Akio M., 1991, U. S. Patent, Patent No. [5,155,108, 5155108]
[3]   A versatile and regioselective synthesis of vicinal azidoalcohols using cross-linked poly(4-vinylpyridine) supported azide ion under solvent-free conditions [J].
Ali, Mohammad ;
Zarchi, Karimi ;
Tarabsaz, Ali .
CHINESE JOURNAL OF POLYMER SCIENCE, 2013, 31 (12) :1660-1669
[4]   Preparation of 2,6-dimethyl-4-arylpyridine-3,5-dicarbonitrile:: A paired electrosynthesis [J].
Batanero, B ;
Barba, F ;
Martín, A .
JOURNAL OF ORGANIC CHEMISTRY, 2002, 67 (07) :2369-2371
[5]   Preparation of trifluoromethyl sulfides or selenides from trifluoromethyl trimethylsilane and thiocyanates or selenocyanates [J].
Billard, T ;
Large, S ;
Langlois, BR .
TETRAHEDRON LETTERS, 1997, 38 (01) :65-68
[6]   Tetrakis(dimethylamino)ethylene (TDAE) mediated addition of difluoromethyl anions to heteroaryl thiocyanates.: A new simple access to heteroaryl-SCF2R derivatives [J].
Billard, T ;
Langlois, BR ;
Médebielle, M .
TETRAHEDRON LETTERS, 2001, 42 (20) :3463-3465
[7]  
Buchel K.H., 1970, Chemie der Pflanzen Schutz-Und Schadlingsbe Kampfungsmittle, P457
[8]   A clay-mediated eco-friendly thiocyanation of indoles and carbazoles [J].
Chakrabarty, M ;
Sarkar, S .
TETRAHEDRON LETTERS, 2003, 44 (44) :8131-8133
[9]   Efficient Thiocyanation of Indoles Using Para-Toluene Sulfonic Acid [J].
Das, Biswanath ;
Kumar, Avula Satya .
SYNTHETIC COMMUNICATIONS, 2010, 40 (03) :337-341
[10]   APPLICATIONS OF COMBINATORIAL TECHNOLOGIES TO DRUG DISCOVERY .1. BACKGROUND AND PEPTIDE COMBINATORIAL LIBRARIES [J].
GALLOP, MA ;
BARRETT, RW ;
DOWER, WJ ;
FODOR, SPA ;
GORDON, EM .
JOURNAL OF MEDICINAL CHEMISTRY, 1994, 37 (09) :1233-1251
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