HETEROGENEOUS AND CATALYTIC THIOCYANATION OF AROMATIC COMPOUNDS IN AQUEOUS MEDIA

被引:33
作者
Zolfigol, Mohammad Ali [1 ]
Khazaei, Ardeshir [1 ]
Mokhlesi, Mohammad [1 ]
Vahedi, Hoshang [2 ]
Sajadifar, Sami [1 ,2 ]
Pirveysian, Mahtab [1 ]
机构
[1] Bu Ali Sina Univ, Fac Chem, Hamadan, Iran
[2] Payame Noor Univ, Dept Chem, Tehran 193954697, Iran
关键词
Silica sulfuric acid; silica boron sulfonic acid; thiocyanation; water; heterogeneous; SILICA SULFURIC-ACID; CARBONYL-COMPOUNDS; SULFONIC-ACID; AMMONIUM THIOCYANATE; ARYL THIOCYANATES; REGIOSELECTIVE THIOCYANATION; ELECTROPHILIC THIOCYANATION; FUNCTIONALIZED SILICA; EFFICIENT; OXIDATION;
D O I
10.1080/10426507.2011.610846
中图分类号
O61 [无机化学];
学科分类号
070301 ; 081704 ;
摘要
This article describes a highly efficient heterogeneous catalytic thiocyanation of indoles, substituted anilines (electron rich and electron deficient) and N-substituted aromatic amines in water under mild and green conditions. The reaction of substrates with KSCN in the presence of silica sulfuric acid (SSA) and silica boron sulfonic acid (SBSA) as heterogeneous catalysts and H2O2 or UHP (urea hydrogen peroxide) as green oxidants produces aryl thiocyanates in short reaction times and high yields. Moreover, in this article, some novel aryl thiocyanates were synthesized.
引用
收藏
页码:295 / 304
页数:10
相关论文
共 41 条
[1]   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
[2]   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
[3]   A clay-mediated eco-friendly thiocyanation of indoles and carbazoles [J].
Chakrabarty, M ;
Sarkar, S .
TETRAHEDRON LETTERS, 2003, 44 (44) :8131-8133
[4]   Novel and facile transformation of N,N-Disubstituted glycylamides into corresponding cyanamides by using pentavalent iodine reagents in combination with tetraethylammonium bromide [J].
Chaudhari, Kiran H. ;
Mahajan, Ulhas S. ;
Bhalerao, Dinesh S. ;
Akamanchi, Krishnacharya G. .
SYNLETT, 2007, (18) :2815-2818
[5]   Organic reactions catalyzed over solid acids [J].
Corma, A ;
Garcia, H .
CATALYSIS TODAY, 1997, 38 (03) :257-308
[6]   INORGANIC SOLID ACIDS AND THEIR USE IN ACID-CATALYZED HYDROCARBON REACTIONS [J].
CORMA, A .
CHEMICAL REVIEWS, 1995, 95 (03) :559-614
[7]   Sulfonic acid functionalized silica:: A remarkably efficient heterogeneous reusable catalyst for α-monobromination of carbonyl compounds using N-bromosuccinimide [J].
Das, B ;
Venkateswarlu, K ;
Holla, H ;
Krishnaiah, M .
JOURNAL OF MOLECULAR CATALYSIS A-CHEMICAL, 2006, 253 (1-2) :107-111
[8]   Sulfonic acid functionalized silica as an efficient heterogeneous recyclable catalyst for one-pot synthesis of 2-substituted benzimidazoles [J].
Das, Biswanath ;
Kanth, Boddu Shashi ;
Reddy, Kongara Ravinder ;
Kumar, Avula Satya .
JOURNAL OF HETEROCYCLIC CHEMISTRY, 2008, 45 (05) :1499-1502
[9]   Metal-Free Catalytic Oxidation of Urazoles under Mild and Heterogeneous Conditions via Combination of Ammonium Nitrate and Catalytic Amounts of Silica Sulfuric Acid [J].
Ghorbani-Choghamarani, A. ;
Zolfigol, M. A. ;
Hajjami, M. ;
Mallakpour, S. .
JOURNAL OF THE IRANIAN CHEMICAL SOCIETY, 2010, 7 (04) :834-839
[10]   Metal-Free Oxidation of Urazole and 1,4-Dihydropyridine Derivatives Under Mild and Heterogeneous Conditions by Nitro Urea, Derived from Urea Nitrate, and Silica Sulfuric Acid [J].
Ghorbani-Choghamarani, Arash ;
Zolfigol, Mohammad A. ;
Hajjami, Maryam ;
Rastgoo, Shahrbanoo ;
Mallakpour, Shadpour .
LETTERS IN ORGANIC CHEMISTRY, 2010, 7 (03) :249-254