Recent Applications of Doebner, Doebner-von Miller and Knoevenagel-Doebner Reactions in Organic Syntheses

被引:39
作者
Heravi, Majid M. [1 ]
Asadi, Shima [1 ]
Azarakhshi, Fatemeh [2 ]
机构
[1] Alzahra Univ, Dept Chem, Tehran, Iran
[2] Islamic Azad Univ, Dept Chem, Varamin Pishva Branch, Varamin, Iran
关键词
Doebner reaction; doebner-von miller; heterocyclic syntheses; Knoevenagel reaction; quinolines; QUINOLINE-4-CARBOXYLIC ACID-DERIVATIVES; QUINOLINE SYNTHESIS; EFFICIENT SYNTHESIS; (E)-ALPHA; BETA-UNSATURATED ESTERS; REGIOSELECTIVE HYDROFORMYLATION; MICROWAVE IRRADIATION; BIOLOGICAL EVALUATION; PRACTICAL SYNTHESIS; FACILE SYNTHESIS; SKRAUP SYNTHESIS;
D O I
10.2174/1570179411666140426003616
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Quinolines as one of the most important classes of heterocyclic compounds are widely present as key structural motifs in many natural products, particularly in alkaloids and numerous bioactive drugs. Various name reactions for the syntheses of quinolines such as Skraup, Camps, Combes, Conrad-Lympach, Knorr, Gould-Jacobs, Povarov, Doebner and Doebner-von Miller, Pfitzinger and Niementowski, and Friedlander have already been discovered and extensively developed and modified. This review covers the most recent applications of Doebner and Doebner-von Miller reactions in organic syntheses. In addition the developments of the Knoevenagel-Doebner reaction in the synthesis of, alpha,beta-unsaturated carboxylic acids were demonstrated. In this paper we provide extensive compilation of the development of the Doebner reaction and variations for the synthesis of quinolines published from 2006 to 2013.
引用
收藏
页码:701 / 731
页数:31
相关论文
共 185 条
[1]   DESIGN, SYNTHESIS, AND PHARMACOLOGICAL ACTIVITIES OF 2-SUBSTITUTED 4-PHENYLQUINOLINES AS POTENTIAL ANTIDEPRESSANT DRUGS [J].
ALHAIDER, AA ;
ABDELKADER, MA ;
LIEN, EJ .
JOURNAL OF MEDICINAL CHEMISTRY, 1985, 28 (10) :1394-1398
[2]   2-AMINOPYRIDINE AND THE DOEBNER REACTION [J].
ALLEN, CFH ;
SPANGLER, FW ;
WEBSTER, ER .
JOURNAL OF ORGANIC CHEMISTRY, 1951, 16 (01) :17-20
[3]  
[Anonymous], 1991, SYNLETT
[4]  
[Anonymous], HETEROCYCLES
[5]   Microwave-enhanced synthesis of N-shifted buflavine analogues via a Suzuki-ring-closing metathesis protocol [J].
Appukkuttan, P ;
Dehaen, W ;
Van der Eycken, E .
ORGANIC LETTERS, 2005, 7 (13) :2723-2726
[6]  
Arctander S, 1969, PERFUME FLAVOR CHEM, VI
[7]  
ARDUINI A, 1981, SYNTHESIS-STUTTGART, P975
[8]   POTENTIAL ANTITUMOR AGENTS .57. 2-PHENYLQUINOLINE-8-CARBOXAMIDES AS MINIMAL DNA-INTERCALATING ANTITUMOR AGENTS WITH INVIVO SOLID TUMOR-ACTIVITY [J].
ATWELL, GJ ;
BAGULEY, BC ;
DENNY, WA .
JOURNAL OF MEDICINAL CHEMISTRY, 1989, 32 (02) :396-401
[9]   gem-dibromomethylarenes:: A convenient substitute for noncommercial aldehydes in the Knoevenagel-Doebner reaction for the synthesis of α,β-unsaturated carboxylic acids [J].
Augustine, John Kallikat ;
Naik, Yanjerappa Arthoba ;
Mandal, Ashis Baran ;
Chowdappa, Nagaraja ;
Praveen, Vinuthan B. .
JOURNAL OF ORGANIC CHEMISTRY, 2007, 72 (25) :9854-9856
[10]   Phenolic and other metabolites of Phellinus pini, a fungus pathogenic to pine [J].
Ayer, WA ;
Muir, DJ ;
Chakravarty, P .
PHYTOCHEMISTRY, 1996, 42 (05) :1321-1324