Clay/Water mixtures - A heterogeneous and ecologically efficient catalyst for the three-component stereoselective synthesis of tetrahydroquinolines

被引：0

作者：

Sartori, G ^{[1
]}

Bigi, F ^{[1
]}

Maggi, R ^{[1
]}

Mazzacani, A ^{[1
]}

Oppici, G ^{[1
]}

机构：

[1] Univ Parma, Dipartimento Chim Organ & Ind, I-43100 Parma, Italy

来源：

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY | 2001年 / 2001卷 / 13期

关键词：

cycloadditions; environmental chemistry; heterogeneous catalysis; multicomponent reactions; Nitrogen heterocycles;

D O I：

10.1002/1099-0690(200107)2001:13<2513::AID-EJOC2513>3.0.CO;2-A

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The three-component synthesis of tetrahydroquinolines 5 from aromatic amines i, aromatic aldehydes 2 and cyclopentadiene (4) can be efficiently performed in water in the presence of the commercially available bentonite Bieliaca. The overall process involves the rapid initial production of the imines 3, which subsequently undergo aza-cycloaddition processes with cyclopentadiene, affording products in good yields and with excellent selectivities. The cycloaddition step is regiospecific and stereospecific, exclusively giving the endo product. It was possible to reuse the catalyst several times without lowering its efficiency. The process represents a clean, safe and environmentally friendly route for the production of a class of natural products displaying a wide range of biological activities.

引用

页码：2513 / 2518

页数：6

共 45 条

[21] ROLE REVERSAL IN THE CYCLOCONDENSATION OF CYCLOPENTADIENE WITH HETERODIENOPHILES DERIVED FROM ARYL AMINES AND ALDEHYDES - SYNTHESIS OF NOVEL TETRAHYDROQUINOLINES
GRIECO, PA
BAHSAS, A
[J]. TETRAHEDRON LETTERS, 1988, 29 (46) : 5855 - 5858
[22] Catalytic asymmetric aza Diels-Alder reactions using a chiral lanthanide Lewis acid. Enantioselective synthesis of tetrahydroquinoline derivatives using a catalytic amount of a chiral source
Ishitani, H
Kobayashi, S
[J]. TETRAHEDRON LETTERS, 1996, 37 (41) : 7357 - 7360
[23] JOH T, 1967, TETRAHEDRON LETT, P4199
[24] 2,4-DIAMINO-5-BENZYLPYRIMIDINES AND ANALOGS AS ANTIBACTERIAL AGENTS .12. 1,2-DIHYDROQUINOLYLMETHYL ANALOGS WITH HIGH-ACTIVITY AND SPECIFICITY FOR BACTERIAL DIHYDROFOLATE-REDUCTASE
JOHNSON, JV
RAUCKMAN, BS
BACCANARI, DP
ROTH, B
[J]. JOURNAL OF MEDICINAL CHEMISTRY, 1989, 32 (08) : 1942 - 1949
[25] Solid support synthesis of polysubstituted tetrahydroquinolines via three-component condensation catalyzed by Yb(OTf)3
Kiselyov, AS
Smith, L
Armstrong, RW
[J]. TETRAHEDRON, 1998, 54 (20) : 5089 - 5096
[26] Immobilized aldehydes and olefins in the solid support synthesis of tetrahydroquinolines via a three component condensation.
Kiselyov, AS
Smith, L
Virgilio, A
Armstrong, RW
[J]. TETRAHEDRON, 1998, 54 (28) : 7987 - 7996
[27] KOBAYASHI S, 1995, SYNLETT, P233
[28] A polymer-supported scandium catalyst
Kobayashi, S
Nagayama, S
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1996, 61 (07) : 2256 - 2257
[29] A new methodology for combinatorial synthesis. Preparation of diverse quinoline derivatives using a novel polymer-supported scandium catalyst
Kobayashi, S
Nagayama, S
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1996, 118 (37) : 8977 - 8978
[30] KOBAYASHI S, 1995, SYNTHESIS-STUTTGART, P1195

← 1 2 3 4 5 →