Solid support synthesis of polysubstituted tetrahydroquinolines via three-component condensation catalyzed by Yb(OTf)3

被引：90

作者：

Kiselyov, AS ^{[1
]}

Smith, L ^{[1
]}

Armstrong, RW ^{[1
]}

机构：

[1] Amgen Inc, Small Mol Drug Discovery, Thousand Oaks, CA 91320 USA

来源：

TETRAHEDRON | 1998年 / 54卷 / 20期

关键词：

D O I：

10.1016/S0040-4020(98)00248-8

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Solid support synthesis of polysubstituted tetrahydroquinolines is described. The procedure is based on a three-component condensation involving immobilized derivatives of 4-aminophenylalanine, aldehydes, alkenes and Yb(OTf)(3) as a catalyst. The methodology is further expanded to the solid support synthesis of tricyclic tetrahydroquinoline by the concomitant formation of the Schiff base followed by intramolecular trap of the alkene. (C) 1998 Elsevier Science Ltd. All rights reserved.

引用

页码：5089 / 5096

页数：8

共 44 条

[21] A polymer-supported scandium catalyst [J].

Kobayashi, S ;

Nagayama, S .

JOURNAL OF ORGANIC CHEMISTRY, 1996, 61 (07) :2256-2257

[22] A new methodology for combinatorial synthesis. Preparation of diverse quinoline derivatives using a novel polymer-supported scandium catalyst [J].

Kobayashi, S ;

Nagayama, S .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1996, 118 (37) :8977-8978

[23]

KOBAYASHI S, 1995, SYNTHESIS-STUTTGART, P1095

[24] PARTITIONING OF OXAMNIQUINE INTO BRAIN-TISSUE FOLLOWING INTRAVENOUS ADMINISTRATION TO FEMALE WISTAR RATS [J].

KOKWARO, GO ;

TAYLOR, G .

DRUG AND CHEMICAL TOXICOLOGY, 1990, 13 (04) :347-354

[25] INTRAMOLECULAR HETERO-DIELS-ALDER REACTION OF N-ARYLIMINES - APPLICATIONS TO THE SYNTHESIS OF OCTAHYDROACRIDINE DERIVATIVES [J].

LASCHAT, S ;

LAUTERWEIN, J .

JOURNAL OF ORGANIC CHEMISTRY, 1993, 58 (10) :2856-2861

[26] NOVEL (IMINO-ETA(6)-ARENE)CHROMIUM COMPLEXES AND THEIR DIASTEREOSELECTIVE INTRAMOLECULAR HETERO-DIELS-ALDER REACTIONS [J].

LASCHAT, S ;

NOE, R ;

RIEDEL, M ;

KRUGER, C .

ORGANOMETALLICS, 1993, 12 (09) :3738-3742

[27] 4-AMIDO-2-CARBOXYTETRAHYDROQUINOLINES - STRUCTURE-ACTIVITY-RELATIONSHIPS FOR ANTAGONISM AT THE GLYCINE SITE OF THE NMDA RECEPTOR [J].

LEESON, PD ;

CARLING, RW ;

MOORE, KW ;

MOSELEY, AM ;

SMITH, JD ;

STEVENSON, G ;

CHAN, T ;

BAKER, R ;

FOSTER, AC ;

GRIMWOOD, S ;

KEMP, JA ;

MARSHALL, GR ;

HOOGSTEEN, K .

JOURNAL OF MEDICINAL CHEMISTRY, 1992, 35 (11) :1954-1968

[28] CYCLO-ADDITION REACTIONS OF ALPHA-KETO IMINES - REGIOSELECTIVITIES AND STEREOSELECTIVITIES IN THE DIENIC AND DIENOPHILIC ADDITIONS TO CONJUGATED DIENES [J].

LUCCHINI, V ;

PRATO, M ;

SCORRANO, G ;

TECILLA, P .

JOURNAL OF ORGANIC CHEMISTRY, 1988, 53 (10) :2251-2258

[29] REACTION OF ELECTRON-RICH ALKENES WITH ANILINES AND FORMALDEHYDE - SYNTHESES OF TETRAHYDROQUINOLINES [J].

MELLOR, JM ;

MERRIMAN, GD .

TETRAHEDRON, 1995, 51 (21) :6115-6132

[30]

MELLOR JM, 1991, TETRAHEDRON LETT, V32, P6115

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