Recent synthetic developments in a powerful imino Diels-Alder reaction (Povarov reaction): application to the synthesis of N-polyheterocycles and related alkaloids

被引：484

作者：

Kouznetsov, Vladimir V. ^{[1
]}

机构：

[1] Univ Ind Santander, Lab Quim Organ & Biomol, CIBIMOL, Bucaramanga 678, Colombia

来源：

TETRAHEDRON | 2009年 / 65卷 / 14期

关键词：

Intra- and intermolecular imino; Diets-Alder reaction; Povarov reaction; Cycloaddition; Quinoline derivatives; Polyheterocycles; Alkaloids; ONE-POT SYNTHESIS; HIGHLY DIASTEREOSELECTIVE SYNTHESIS; CATALYZED INTRAMOLECULAR CYCLIZATION; 3-COMPONENT COUPLING PROTOCOL; 4+2 CYCLOADDITION REACTIONS; ASYMMETRIC TOTAL-SYNTHESIS; ANTICANCER DRUG TAS-103; SOLID SUPPORT SYNTHESIS; ONE-STEP SYNTHESIS; QUINOLINE DERIVATIVES;

D O I：

10.1016/j.tet.2008.12.059

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

[No abstract available]

引用

页码：2721 / 2750

页数：30

共 238 条

[1] Synthesis of aryl-substituted quinoline derivatives via Bronsted acid-catalyzed [4+2] aza Diels-Alder reaction [J].

Akiyama, T ;

Nakashima, S ;

Yokota, K ;

Fuchibe, K .

CHEMISTRY LETTERS, 2004, 33 (07) :922-923

[2] Lewis acid promoted [4+2] annulation of allylsilane and allylgermane with aldimine; Preparation of tetrahydroquinolines [J].

Akiyama, T ;

Suzuki, M ;

Kagoshima, H .

HETEROCYCLES, 2000, 52 (02) :529-532

[3] Chiral Bronsted acid-catalyzed inverse electron-demand aza Diels-Alder reaction [J].

Akiyama, Takahiko ;

Morita, Hisashi ;

Fuchibe, Kohei .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2006, 128 (40) :13070-13071

[4] Regio- and stereo-selective aza-Diels-Alder reaction of ethyl glyoxylate 4-methoxyphenylimine with 1,3-dienes in the presence of BF3•Et2O.: Evidence for a non-concerted mechanism [J].

Alves, M. Jose ;

Azoia, Nuno G. ;

Fortes, A. Gil .

TETRAHEDRON, 2007, 63 (03) :727-734

[5] Triphenylphosphonium perchlorate as an efficient catalyst for mono- and bis-intramolecular imino Diels-Alder reactions: synthesis of tetrahydrochromanoquinolines [J].

Anniyappan, M ;

Muralidharan, D ;

Perumal, PT .

TETRAHEDRON LETTERS, 2003, 44 (18) :3653-3657

[6] A new multicomponent synthesis of 1,2,3,4-tetrahydroquinolines [J].

Annunziata, R ;

Cinquini, M ;

Cozzi, F ;

Molteni, V ;

Schupp, O .

TETRAHEDRON, 1997, 53 (28) :9715-9726

[7]

Annunziata R, 2002, EUR J ORG CHEM, V2002, P1184

[8]

[Anonymous], 1987, Hetero Diels Alder methodology in Organic Synthesis

[9]

[Anonymous], STUDIES NATURAL PROD

[10] SYNTHESIS OF 6-(4-METHYL-1-PIPERAZINYL)-7H-INDENO[2,1-C]QUINOLINE DERIVATIVES AS POTENTIAL 5-HT RECEPTOR LIGANDS [J].

ANZINI, M ;

CAPPELLI, A ;

VOMERO, S .

JOURNAL OF HETEROCYCLIC CHEMISTRY, 1991, 28 (07) :1809-1812

← 1 2 3 4 5 6 7 8 9 10 →