One-pot multicomponent synthesis of highly substituted bicyclo[2.2.2]octane derivatives using bismuth nitrate as a catalyst

被引：7

作者：

Gein, Vladimir L. ^{[1
]}

Yankin, Andrei N. ^{[1
]}

Nosova, Natalia V. ^{[1
]}

Dmitriev, Maxim V. ^{[2
]}

Slepukhin, Pavel A. ^{[3
]}

机构：

[1] Perm State Pharmaceut Acad, Polevaya St 2, Perm, Russia

[2] Perm State Univ, Bukireva St 15, Perm, Russia

[3] Russian Acad Sci, Ural Branch, Inst Organ Synth, Sofya Kovalevskaya St 22-20, Ekaterinburg, Russia

来源：

TETRAHEDRON LETTERS | 2016年 / 57卷 / 22期

关键词：

One-pot synthesis; Multicomponent reaction; Bicyclo[2.2.2]octane derivatives; Bismuth nitrate; Acetoacetanilide; ECONOMIC PASE SYNTHESIS; DIASTEREOSELECTIVE SYNTHESIS; FUNCTIONALIZED PIPERIDINES; ANTIPROTOZOAL ACTIVITIES; AROMATIC-ALDEHYDES; CHIRAL LIGANDS; EFFICIENT; 5-COMPONENT; FACILE; ATOM;

D O I：

10.1016/j.tetlet.2016.04.082

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The one-pot synthesis of novel 3-(arylamino)-5,8-diaryl-1-hydroxy-N-2,N-6-diphenylbicyclo[2.2.2]oct-2-ene-2,6-dicarboxamides in good yields has been accomplished via the multicomponent reaction of aromatic aldehydes, substituted anilines, and acetoacetanilide using bismuth nitrate as a catalyst. (C) 2016 Elsevier Ltd. All rights reserved.

引用

页码：2441 / 2444

页数：4

共 69 条

[1] Diastereoselective Synthesis of ß-Lactam-Oxindole Hybrids Through a Three-Component Reaction of Azetidine-2,3-diones, a-Diazo-oxindoles, and Alcohols Catalyzed by [Rh2(OAc)4] [J].

Alcaide, Benito ;

Almendros, Pedro ;

Aragoncillo, Cristina ;

Callejo, Ricardo ;

Pilar Ruiz, M. ;

Rosario Torres, M. .

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2012, 2012 (12) :2359-2366

[2] Ultrasound-assisted bismuth nitrate-induced green synthesis of novel pyrrole derivatives and their biological evaluation as anticancer agents [J].

Bandyopadhyay, Debasish ;

Mukherjee, Sanghamitra ;

Granados, Jose C. ;

Short, John D. ;

Banik, Bimal K. .

EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, 2012, 50 :209-215

[3] Microwave-induced bismuth nitrate-catalyzed synthesis of dihydropyrimidones via Biginelli condensation under solventless conditions [J].

Banik, Birnal K. ;

Reddy, Anupama T. ;

Datta, Arup ;

Mukhopadhyay, Chhanda .

TETRAHEDRON LETTERS, 2007, 48 (41) :7392-7394

[4] Antiprotozoal activities of new bis-chlorophenyl derivatives of bicyclic octanes and aza-nonanes [J].

Berger, Heinrich ;

Seebacher, Werner ;

Saf, Robert ;

Kaiser, Marcel ;

Brun, Reto ;

Weis, Robert .

BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2006, 16 (20) :5457-5461

[5] Efficient preparation of the isoindoline framework via a six component, tandem double A3-coupling and [2+2+2] cycloaddition reaction [J].

Bonfield, E. Ryan ;

Li, Chao-Jun .

ADVANCED SYNTHESIS & CATALYSIS, 2008, 350 (03) :370-374

[6] Applications of bismuth(III) compounds in organic synthesis [J].

Bothwell, Jason M. ;

Krabbe, Scott W. ;

Mohan, Ram S. .

CHEMICAL SOCIETY REVIEWS, 2011, 40 (09) :4649-4707

[7] Bismuth nitrate-catalyzed multicomponent reaction for efficient and one-pot synthesis of densely functionalized piperidine scaffolds at room temperature [J].

Brahmachari, Goutam ;

Das, Suvankar .

TETRAHEDRON LETTERS, 2012, 53 (12) :1479-1484

[8] Synthesis of rhodium(I) complexes with the new dithiol chiral ligand (+)-trans-2,3-bis(mercaptomethyl)-bicyclo[2.2.2]octane (H2BCOS) - Their application as catalysts precursors in the styrene hydroformylation [J].

CastellanosPaez, A ;

Castillon, S ;

Claver, C .

JOURNAL OF ORGANOMETALLIC CHEMISTRY, 1997, 539 (1-2) :1-7

[9] Tandem and domino catalytic strategies for enantioselective synthesis [J].

Chapman, Christopher J. ;

Frost, Christopher G. .

SYNTHESIS-STUTTGART, 2007, (01) :1-21

[10] Pot, Atom, and Step Economic (PASE) Synthesis of Highly Substituted Piperidines: A Five-Component Condensation [J].

Clarke, Paul A. ;

Zaytsev, Andrey V. ;

Whitwood, Adrian C. .

SYNTHESIS-STUTTGART, 2008, (21) :3530-3532

← 1 2 3 4 5 6 7 →