Proline-Catalyzed Simple and Efficient Synthesis of 1,8-Dioxo-decahydroacridines in Aqueous Ethanol Medium

被引：109

作者：

Venkatesan, K. ^{[1
]}

Pujari, Suresh S. ^{[1
]}

Srinivasan, Kumar V. ^{[1
]}

机构：

[1] Natl Chem Lab, Div Organ Chem Technol, Pune 411008, Maharashtra, India

来源：

SYNTHETIC COMMUNICATIONS | 2009年 / 39卷 / 02期

关键词：

Aqueous media; 1; 8-dioxodecahydroacridines; one-pot MCR; proline; ACIDIC IONIC LIQUID; DERIVATIVES; NIFEDIPINE; ACRIDINE; WATER;

D O I：

10.1080/00397910802044306

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Proline-catalyzed synthesis of 1,8-dioxo-decahydroacridines is achieved via one-pot, three-component condensation of aromatic aldehydes, cyclic diketone, and aryl amines in aqueous ethanol medium. This method offers the advantages of proceeding in neutral and mild conditions, giving high to excellent yields of acridines with easy workup procedure.

引用

页码：228 / 241

页数：14

共 15 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] 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

[4] The first synthesis of the pentacyclic pyridoacridine marine alkaloids: Arnoamines A and B [J].

Delfourne, E ;

Roubin, C ;

Bastide, J .

JOURNAL OF ORGANIC CHEMISTRY, 2000, 65 (18) :5476-5479

[5] Synthesis and antiproliferative activity of some variously substituted acridine and azacridine derivatives [J].

Ferlin, MG ;

Marzano, C ;

Chiarelotto, G ;

Baccichetti, F ;

Bordin, F .

EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, 2000, 35 (09) :827-837

[6] Ionic liquid promoted novel and efficient one pot synthesis of 3,4-dihydropyrimidin-2-(1H)-ones at ambient temperature under ultrasound irradiation [J].

Gholap, AR ;

Venkatesan, K ;

Daniel, T ;

Lahoti, RJ ;

Srinivasan, KV .

GREEN CHEMISTRY, 2004, 6 (03) :147-150

[7]

GUAZZI M, 1977, CLIN PHARMACOL THER, V22, P528

[8]

Li C.J., 1997, ORGANIC REACTIONS AQ

[9] Stereoselective organic reactions in water [J].

Lindström, UM .

CHEMICAL REVIEWS, 2002, 102 (08) :2751-2771

[10] Proline-catalyzed asymmetric reactions [J].

List, B .

TETRAHEDRON, 2002, 58 (28) :5573-5590

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