Recent Syntheses of 1,2,3,4-Tetrahydroquinolines, 2,3-Dihydro-4(1H)-quinolinones and 4(1H)-Quinolinones using Domino Reactions

被引：117

作者：

Nammalwar, Baskar ^{[1
]}

Bunce, Richard A. ^{[1
]}

机构：

[1] Oklahoma State Univ, Dept Chem, Stillwater, OK 74078 USA

来源：

MOLECULES | 2014年 / 19卷 / 01期

关键词：

domino reaction; tandem reaction; cascade reaction; 1,2,3,4-tetrahydroquinoline; 2,3-dihydro-4(1H)-quinolinone; 4(1H)-quinolinone; heterocycle synthesis; drug synthesis; REDUCTIVE AMINATION REACTION; SOLID-PHASE SYNTHESIS; MOLECULE RENIN INHIBITORS; MICHAEL ADDITION-REACTION; FRIEDEL-CRAFTS ACYLATION; MALONIC-ACID ESTER; DIASTEREOSELECTIVE SYNTHESIS; QUINOLONE-ALKALOIDS; EVODIA-RUTAECARPA; DISCORHABDIN-C;

D O I：

10.3390/molecules19010204

中图分类号：

Q5 [生物化学]; Q7 [分子生物学];

学科分类号：

071010 ; 081704 ;

摘要：

A review of the recent literature is given focusing on synthetic approaches to 1,2,3,4-tetrahydroquinolines, 2,3-dihydro-4(1H)-quinolinones and 4(1H)-quinolinones using domino reactions. These syntheses involve: (1) reduction or oxidation followed by cyclization; (2) SNAr-terminated sequences; (3) acid-catalyzed ring closures or rearrangements; (4) high temperature cyclizations and (5) metal-promoted processes as well as several less thoroughly studied reactions. Each domino method is presented with a brief discussion of mechanism, scope, yields, simplicity and potential utility.

引用

页码：204 / 232

页数：29

共 134 条

[11] Helquinoline, a new tetrahydroquinoline antibiotic from Janibacter limosus Hel 1 [J].

Asolkar, RN ;

Schröder, D ;

Heckmann, R ;

Lang, S ;

Wagner-Döbler, I ;

Laatsch, H .

JOURNAL OF ANTIBIOTICS, 2004, 57 (01) :17-23

[12] A stereodivergent synthesis of virantmycin by an enzyme-mediated diester desymmetrization and a highly hindered aryl amination [J].

Back, TG ;

Wulff, JE .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2004, 43 (47) :6493-6496

[13] Recent Advances in the Synthesis of Indole and Quinoline Derivatives through Cascade Reactions [J].

Barluenga, Jose ;

Rodriguez, Felix ;

Fananas, Francisco J. .

CHEMISTRY-AN ASIAN JOURNAL, 2009, 4 (07) :1036-1048

[14]

Barrett J F, 2000, Curr Opin Investig Drugs, V1, P45

[15]

Basuri TS, 2011, J PHARM RES, V4, P1294

[16]

Baumgarth M., 1995, Preparation of (Benzocyclylethyl)arylpiperidines and-Piperazines for Treating Arrhythmia and Tachycardia, Patent No. [DE4321366A1, 4321366]

[17] THE METHODS OF SYNTHESIS, MODIFICATION, AND BIOLOGICAL ACTIVITY OF 4-QUINOLONES (REVIEW) [J].

Boteva, A. A. ;

Krasnykh, O. P. .

CHEMISTRY OF HETEROCYCLIC COMPOUNDS, 2009, 45 (07) :757-785

[18] Diastereoselective synthesis of linear-fused tricyclic nitrogen heterocycles by a tandem reduction-reductive amination reaction [J].

Bunce, RA ;

Herron, DM ;

Lewis, JR ;

Kotturi, SV ;

Holt, EM .

JOURNAL OF HETEROCYCLIC CHEMISTRY, 2003, 40 (01) :101-106

[19] Diastereoselective synthesis of substituted tetrahydroquinoline-4-carboxylic esters by a tandem reduction-reductive amination reaction [J].

Bunce, RA ;

Herron, DM ;

Johnson, LB ;

Kotturi, SV .

JOURNAL OF ORGANIC CHEMISTRY, 2001, 66 (08) :2822-2827

[20] Aryl-fused nitrogen heterocycles by a tandem reduction-Michael addition reaction [J].

Bunce, RA ;

Herron, DM ;

Ackerman, ML .

JOURNAL OF ORGANIC CHEMISTRY, 2000, 65 (09) :2847-2850

← 1 2 3 4 5 6 7 8 9 10 →