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
Adams, JD
Chang, ML
Klaidman, L
[J]. 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
BENKERT, O
GRUNDER, G
WETZEL, H
[J]. 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
Brahmachari, Goutam
Das, Suvankar
[J]. 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
BRAVI, D
DAVIS, TL
MOURADIAN, MM
CHASE, TN
[J]. MOVEMENT DISORDERS, 1993, 8 (02) : 195 - 197
[7] Systematic structure-based design and stereoselective synthesis of novel multisubstituted cyclopentane derivatives with potent antiinfluenza activity
Chand, P
Kotian, PL
Dehghani, A
El-Kattan, Y
Lin, TH
Hutchison, TL
Babu, YS
Bantia, S
Elliott, AJ
Montgomery, JA
[J]. JOURNAL OF MEDICINAL CHEMISTRY, 2001, 44 (25) : 4379 - 4392
[8] Proline-threonine dipeptide as an organocatalyst for the direct asymmetric aldol reaction
Chandrasekhar, Srivari
Johny, Kancharla
Reddy, Chada Raji
[J]. TETRAHEDRON-ASYMMETRY, 2009, 20 (15) : 1742 - 1745
[9] Pot, Atom, and Step Economic (PASE) Synthesis of Highly Substituted Piperidines: A Five-Component Condensation
Clarke, Paul A.
Zaytsev, Andrey V.
Whitwood, Adrian C.
[J]. SYNTHESIS-STUTTGART, 2008, (21): : 3530 - 3532
[10] Pot, atom and step economic (PASE) synthesis of highly functionalized piperidines: a five-component condensation
Clarke, Paul A.
Zaytzev, Andrey V.
Whtwoo, Adrian C.
[J]. TETRAHEDRON LETTERS, 2007, 48 (30) : 5209 - 5212

← 1 2 3 4 5 6 →