Aza-Diels-Alder reaction of Danishefsky's diene with immines catalyzed by porous α-zirconium hydrogen phosphate and SDS under solvent-free conditions

被引：23
作者：
Bellezza, Francesca
Cipiciani, Antonio
Costantino, Umberto
Fringuelli, Francesco
Orru, Mara
Piermatti, Oriana [1 ]
Pizzo, Ferdinando
机构：
[1] Univ Perugia, Dipartimento Chim, I-06123 Perugia, Italy
来源：
CATALYSIS TODAY | 2010年 / 152卷 / 1-4期
关键词：
Bronsted-acid catalysis; Heterogeneous catalysis; Zirconium phosphate; Aza-Diels-Alder reaction; Solvent-free conditions; INSOLUBLE ACID SALTS; TETRAVALENT METALS; EFFICIENT CATALYST; ORGANIC-SYNTHESIS; ION-EXCHANGE; IMINES; WATER; THIOLYSIS; TRIFLATE; CONDENSATIONS;
D O I：
10.1016/j.cattod.2009.07.105
中图分类号：
O69 [应用化学];
学科分类号：
081704 ;
摘要：
The aza-Diels-Alder reaction between benzaldimines 1 and Danishefsky's diene in solvent-free conditions is reported for the first time. The reaction occurs rapidly at 30 degrees C and is catalyzed by porous alpha-zirconium hydrogen phosphate (p-alpha ZrP) in the presence of sodium dodecyl sulfate (SDS). The yields were excellent. The recycling of the catalyst has also been investigated. (C) 2009 Elsevier B.V. All rights reserved.
引用
收藏
页码：61 / 65
页数：5
相关论文
共 67 条
[1]   Bronsted acid-catalyzed aza Diels-Alder reaction of Danishefsky's diene with aldimine generated in situ from aldehyde and amine in aqueous media [J].
Akiyama, T ;
Takaya, J ;
Kagoshima, H .
TETRAHEDRON LETTERS, 1999, 40 (44) :7831-7834
[2]   Stronger bronsted acids [J].
Akiyama, Takahiko .
CHEMICAL REVIEWS, 2007, 107 (12) :5744-5758
[3]   Recent progress in chiral Bronsted acid catalysis [J].
Akiyama, Takahiko ;
Itoh, Junji ;
Fuchibe, Kohei .
ADVANCED SYNTHESIS & CATALYSIS, 2006, 348 (09) :999-1010
[4]   CRYSTALLINE INSOLUBLE ACID SALTS OF TETRAVALENT METALS .20. FORWARD AND REVERSE CS+-H+ AND RB+-H+ ION-EXCHANGE ON CRYSTALLINE ZIRCONIUM-PHOSPHATE [J].
ALBERTI, G ;
COSTANTINO, U ;
ALLULLI, S ;
MASSUCCI, MA .
JOURNAL OF INORGANIC & NUCLEAR CHEMISTRY, 1975, 37 (7-8) :1779-1786
[5]   Layered and pillared metal(IV) phosphates and phosphonates [J].
Alberti, G ;
Casciola, M ;
Costantino, U ;
Vivani, R .
ADVANCED MATERIALS, 1996, 8 (04) :291-303
[6]  
ALBERTI G, 1980, J INORG NUCL CHEM, V42, P1631, DOI 10.1016/0022-1902(80)80328-9
[7]   Synthesis and applications of chiral bis-THF in asymmetric synthesis [J].
Alexakis, A ;
Tomassini, A ;
Leconte, S .
TETRAHEDRON, 2004, 60 (42) :9479-9484
[8]   Indium triflate - An efficient catalyst for hetero Diels-Alder reactions [J].
Ali, T ;
Chauhan, KK ;
Frost, CG .
TETRAHEDRON LETTERS, 1999, 40 (30) :5621-5624
[9]   Synthesis of 4-aryl-1H-1,2,3-triazoles through TBAF-catalyzed [3+2] cycloaddition of 2-aryl-1-nitroethenes with TMSN3 under solvent-free conditions [J].
Amantini, D ;
Fringuelli, F ;
Piermatti, O ;
Pizzo, F ;
Zunino, E ;
Vaccaro, L .
JOURNAL OF ORGANIC CHEMISTRY, 2005, 70 (16) :6526-6529
[10]   TBAF-Catalyzed synthesis of 5-substituted IH-tetrazoles under solventless conditions [J].
Amantini, D ;
Beleggia, R ;
Fringuelli, F ;
Pizzo, F ;
Vaccaro, L .
JOURNAL OF ORGANIC CHEMISTRY, 2004, 69 (08) :2896-2898
1234567