Melamine Sulfonic Acid: A Recoverable Catalyst for the Ecofriendly Synthesis of Thiocyanohydrins Under Solvent-Free Conditions

被引：18

作者：

Kiasat, Ali Reza ^{[1
]}

Fallah-Mehrjardi, Mehdi ^{[1
]}

机构：

[1] Shahid Chamran Univ, Fac Sci, Dept Chem, Ahvaz 6135743169, Iran

来源：

SYNTHETIC COMMUNICATIONS | 2010年 / 40卷 / 10期

关键词：

Melamine sulfonic acid; ring opening of epoxide; solid acid catalyst; thiocyanohydrin; BETA-HYDROXY THIOCYANATES; PHASE-TRANSFER CATALYST; REGIOSELECTIVE CONVERSION; POLYMERIC CATALYST; EPOXIDES; EFFICIENT; AZIDOLYSIS; OXIRANES; ROUTE; DOWEX;

D O I：

10.1080/00397910903100734

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Melamine sulfonic acid as a novel and efficient solid acid catalyst has been synthesized and used in the ring opening of epoxides under solvent-free conditions. This catalyst afforded the corresponding thiocyanohydrins with good regioselectivity and very short reaction times. The catalyst can be easily separated and reused several times without appreciable loss of activity. The availability and recoverability of the catalyst with easy operation and workup make this method attractive for organic synthesis.

引用

页码：1551 / 1558

页数：8

共 17 条

[1] SELECTIVE NUCLEOPHILIC OPENINGS OF 2,3-EPOXY ALCOHOLS CATALYZED BY PD(PPH3)4 [J].

CHOUDARY, BM ;

RANI, SS ;

KANTAM, ML .

SYNTHETIC COMMUNICATIONS, 1990, 20 (15) :2313-2317

[2] DDQ catalyses the conversion of epoxides to β-hydroxy thiocyanates with NH4SCN [J].

Iranpoor, N ;

Kohmareh, GA .

PHOSPHORUS SULFUR AND SILICON AND THE RELATED ELEMENTS, 1999, 152 :135-139

[3] Regioselective ring opening of epoxides using NH4SCN/silica sulfuric acid: An efficient approach for the synthesis of β-hydroxy thiocyanate under solvent-free conditions [J].

Kiasat, Ali R. ;

Zayadi, Maryam ;

Mehrjardi, Mehdi Fallah .

CHINESE CHEMICAL LETTERS, 2008, 19 (06) :665-668

[4] Dowex as Reusable Acidic Polymeric Catalyst in the Efficient and Regioselective Conversion of Epoxides into β-Hydroxy Thiocyanates under Solvent Free Conditions [J].

Kiasat, Ali Reza ;

Fallah-Mehrjardi, Mehdi .

JOURNAL OF THE CHINESE CHEMICAL SOCIETY, 2008, 55 (05) :1119-1124

[5] PEG-SO3H as soluble acidic polymeric catalyst for regioselective ring opening of epoxides:: A high-efficient synthetic approach to β-hydroxy thiocyanates [J].

Kiasat, Ali Reza ;

Mehrjardi, Mehdi Fallah .

SYNTHETIC COMMUNICATIONS, 2008, 38 (17) :2995-3002

[6] Poly(ethylene glycol) Grafted onto Dowex Resin: An Efficient, Recyclable, and Mild Polymer-Supported Phase Transfer Catalyst for the Regioselective Azidolysis of Epoxides in Water [J].

Kiasat, Ali Reza ;

Badri, Rashid ;

Zargar, Behrouz ;

Sayyahi, Soheil .

JOURNAL OF ORGANIC CHEMISTRY, 2008, 73 (21) :8382-8385

[7] B(HSO4)3: a Novel and Efficient Solid Acid Catalyst for the Regioselective Conversion of Epoxides to Thiocyanohydrins under Solvent-Free Conditions [J].

Kiasat, Ali Reza ;

Fallah-Mehrjardi, Mehdi .

JOURNAL OF THE BRAZILIAN CHEMICAL SOCIETY, 2008, 19 (08) :1595-1599

[8] Polyethylene glycol immobilized on silica gel as a new solid-liquid phase-transfer catalyst for regioselective azidolysis of epoxides in water: An efficient route to 1,2-azido alcohols [J].

Kiasat, Ali-Reza ;

Zayadi, Maryam .

CATALYSIS COMMUNICATIONS, 2008, 9 (10) :2063-2067

[9] Solvent-free conversion of oxiranes to thiiranes with thiourea [J].

Kiasat, AR ;

Kazemi, F ;

Jardi, MFM .

PHOSPHORUS SULFUR AND SILICON AND THE RELATED ELEMENTS, 2004, 179 (09) :1841-1844

[10] Al(HSO4)3 as an efficient catalyst for acetalization of carbonyl compounds under heterogeneous or solvent-free conditions [J].

Mirjalili, BF ;

Zolfigol, MA ;

Bamoniri, A ;

Hazar, A .

JOURNAL OF THE BRAZILIAN CHEMICAL SOCIETY, 2005, 16 (04) :877-880

← 1 2 →