Trityl chloride as an efficient organic catalyst for one-pot, five-component and diastereoselective synthesis of highly substituted piperidines

被引：33

作者：

Sajadikhah, Seyed Sajad ^{[1
]}

Hazeri, Nourallah ^{[1
]}

Maghsoodlou, Malek Taher ^{[1
]}

Habibi-Khorassani, Sayyed Mostafa ^{[1
]}

Willis, Anthony C. ^{[2
]}

机构：

[1] Univ Sistan & Baluchestan, Dept Chem, Fac Sci, Zahedan, Iran

[2] Australian Natl Univ, Res Sch Chem, Canberra, ACT 0200, Australia

来源：

RESEARCH ON CHEMICAL INTERMEDIATES | 2014年 / 40卷 / 02期

关键词：

Trityl chloride; Piperidine; beta-Ketoester; Aldehyde; Amine; ECONOMIC PASE SYNTHESIS; FUNCTIONALIZED PIPERIDINES; STEREOSELECTIVE-SYNTHESIS; MULTICOMPONENT REACTIONS; PARKINSONS-DISEASE; CONCISE SYNTHESIS; FACILE ACCESS; INHIBITORS; DOPAMINE; DERIVATIVES;

D O I：

10.1007/s11164-012-0997-8

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Trityl chloride is used as an efficient organic catalyst for the one-pot, five-component and diastereoselective synthesis of highly substituted piperidines by means of reaction between aromatic aldehydes, amines and beta-ketoesters in methanol at 50 A degrees C. The structure as well as relative stereochemistry of products was confirmed by single X-ray crystallographic analysis. This homogeneous catalyst procedure includes some important aspects like the easy work-up, diastereoselectivity, simple and readily available precursors, inexpensive catalyst, relatively short reaction time, and good to high yields.

引用

页码：723 / 736

页数：14

共 60 条

[1] Parkinson's disease - Redox mechanisms [J].

Adams, JD ;

Chang, ML ;

Klaidman, L .

CURRENT MEDICINAL CHEMISTRY, 2001, 8 (07) :809-814

[2]

Bachmann W. E., 1955, ORG SYNTH, V3, P841

[3] DOPAMINE AUTORECEPTOR AGONISTS IN THE TREATMENT OF SCHIZOPHRENIA AND MAJOR DEPRESSION [J].

BENKERT, O ;

GRUNDER, G ;

WETZEL, H .

PHARMACOPSYCHIATRY, 1992, 25 (06) :254-260

[4] 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

[5]

Braun A., 2006, [No title captured], Patent No. [WO 2006/021565, 2006021565]

[6] TREATMENT OF PARKINSONS-DISEASE WITH THE PARTIAL DOPAMINE AGONIST EMD 49980 [J].

BRAVI, D ;

DAVIS, TL ;

MOURADIAN, MM ;

CHASE, TN .

MOVEMENT DISORDERS, 1993, 8 (02) :195-197

[7] Systematic structure-based design and stereoselective synthesis of novel multisubstituted cyclopentane derivatives with potent antiinfluenza activity [J].

Chand, P ;

Kotian, PL ;

Dehghani, A ;

El-Kattan, Y ;

Lin, TH ;

Hutchison, TL ;

Babu, YS ;

Bantia, S ;

Elliott, AJ ;

Montgomery, JA .

JOURNAL OF MEDICINAL CHEMISTRY, 2001, 44 (25) :4379-4392

[8] Proline-threonine dipeptide as an organocatalyst for the direct asymmetric aldol reaction [J].

Chandrasekhar, Srivari ;

Johny, Kancharla ;

Reddy, Chada Raji .

TETRAHEDRON-ASYMMETRY, 2009, 20 (15) :1742-1745

[9] 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

[10] Pot, atom and step economic (PASE) synthesis of highly functionalized piperidines: a five-component condensation [J].

Clarke, Paul A. ;

Zaytzev, Andrey V. ;

Whtwoo, Adrian C. .

TETRAHEDRON LETTERS, 2007, 48 (30) :5209-5212

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