Silica-bonded N-Propyl Sulfamic Acid: A Recyclable Catalyst for the Synthesis of 1,8-Dioxo-decahydroacridines, 1,8-Dioxo-octahydroxanthenes and Quinoxalines

被引：92

作者：

Rashedian, Fatemeh ^{[2
]}

Saberi, Dariush ^{[1
]}

Niknam, Khodabakhsh ^{[1
]}

机构：

[1] Persian Gulf Univ, Fac Sci, Dept Chem, Bushehr 75169, Iran

[2] Islamic Azad Univ, Gachsaran Branch, Dept Chem, Gachsaran, Iran

来源：

JOURNAL OF THE CHINESE CHEMICAL SOCIETY | 2010年 / 57卷 / 5A期

关键词：

Silica-bonded N-propyl sulfamic acid; Acridines; Xanthenes; Dimedone; Quinoxalines; Aldehydes; S-SULFONIC ACID; P-DODECYLBENEZENESULFONIC ACID; HYDROGEN SULFATES M(HSO4)(N); SULFURIC-ACID; HETEROGENEOUS CONDITIONS; EFFICIENT CATALYSTS; REUSABLE CATALYST; TANDEM OXIDATION; CLEAN SYNTHESIS; IONIC LIQUID;

D O I：

10.1002/jccs.201000139

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Silica bonded N-propyl sulfamic acid (SBNPSA) is employed as a solid acid catalyst for the synthesis of 1,8-dioxo-decahydroacridines and 1,8-dioxo-octahydroxanthenes in high yields and short reaction times in ethanol under reflux conditions. Also, this solid acid catalyzed the reaction of 1,2-diamino compounds with 1,2-dicarbonyl compounds for the synthesis of quinoxaline derivatives at room temperature. The catalyst could be recycled and reused several times without any loss of efficiency.

引用

页码：998 / 1006

页数：9

共 75 条

[1] NIFEDIPINE THERAPY FOR CORONARY-ARTERY SPASM - EXPERIENCE IN 127 PATIENTS [J].

ANTMAN, E ;

MULLER, J ;

GOLDBERG, S ;

MACALPIN, R ;

RUBENFIRE, M ;

TABATZNIK, B ;

LIANG, CS ;

HEUPLER, F ;

ACHUFF, S ;

REICHEK, N ;

GELTMAN, E ;

KERIN, NZ ;

NEFF, RK ;

BRAUNWALD, E .

NEW ENGLAND JOURNAL OF MEDICINE, 1980, 302 (23) :1269-1273

[2] Synthesis, antitumor cytotoxicity, and DNA-binding of novel N-5,2-di(ω-aminoalkyl)-2,6-dihydropyrazolo[3,4,5-kl]acridine-5-carboxamides [J].

Antonini, I ;

Polucci, P ;

Magnano, A ;

Martelli, S .

JOURNAL OF MEDICINAL CHEMISTRY, 2001, 44 (20) :3329-3333

[3] Direct and catalytic synthesis of quinoxaline derivatives from epoxides and ene-1,2-diamines [J].

Antoniotti, S ;

Duñach, E .

TETRAHEDRON LETTERS, 2002, 43 (22) :3971-3973

[4]

Brown D J., 2004, The Chemistry of Heterocyclic Compounds

[5] Tris(pentafluorophenyl)borane-catalyzed three-component reaction for the synthesis of 1,8-dioxodecahydroacridines under solvent-free conditions [J].

Chandrasekhar, Srivari ;

Rao, Yaragorla Srinivasa ;

Sreelakshmi, Lella ;

Mahipal, Bodugam ;

Reddy, Chada Raji .

SYNTHESIS-STUTTGART, 2008, (11) :1737-1740

[6] Copper-catalyzed oxidative cyclization of α-hydroxyketones with o-phenylenediamines leading to quinoxalines [J].

Cho, Chan Sik ;

Oh, Sung Gi .

JOURNAL OF MOLECULAR CATALYSIS A-CHEMICAL, 2007, 276 (1-2) :205-210

[7] Catalytic properties of several palladium complexes covalently anchored onto silica for the aerobic oxidation of alcohols [J].

Choudhary, D ;

Paul, S ;

Rajive, GA ;

Clark, JH .

GREEN CHEMISTRY, 2006, 8 (05) :479-482

[8] Laterally-extended porphyrin systems incorporating a switchable unit [J].

Crossley, MJ ;

Johnston, LA .

CHEMICAL COMMUNICATIONS, 2002, (10) :1122-1123

[9] 1-methylimidazolium triflouroacetate ([Hmim]TFA): An efficient reusable acidic ionic liquid for the synthesis of 1,8-dioxo-octahydroxanthenes and 1,8-dioxo-decahydroacridines [J].

Dabiri, Minoo ;

Baghbanzadeh, Mostafa ;

Arzroomchilar, Sham .

CATALYSIS COMMUNICATIONS, 2008, 9 (05) :939-942

[10]

Dailey S, 2001, J MATER CHEM, V11, P2238, DOI 10.1039/b104674h

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