Cascade Synthesis of 3-Quinolinecarboxylic Ester via Benzylation/Propargylation-Cyclization

被引：62
作者：
Fan, Jinmin
Wan, Changfeng
Sun, Gaojun
Wang, Zhiyong [1 ]
机构：
[1] Univ Sci & Technol China, Hefei Natl Lab Phys Sci Microscale, Joint Lab Green Synthet Chem, Hefei 230026, Anhui, Peoples R China
来源：
JOURNAL OF ORGANIC CHEMISTRY | 2008年 / 73卷 / 21期
关键词：
D O I：
10.1021/jo8017654
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
Reactions of 2-amino-aryl alcohols with beta-ketoesters catalyzed by a catalytic amout of FeCl3 via tandem benzylation-cyclization produce the corresponding 3-quinolinecarboxylic esters in good to high yields. Extending this methodology to propargylation-cyclization, 2-nitrophenyl proparoyl alcohols with beta-ketoesters catalyzed by FeCl3 and SnCl, also produce the 4-alkyne-3-quitiolinecarboxylic esters. The mechanistic details of this benzylation/proparoylation and cyclization cascade process are also discussed.
引用
收藏
页码：8608 / 8611
页数：4
相关论文
共 65 条
[1]   A new green approach to the Friedlander synthesis of quinolines [J].
Arcadi, A ;
Chiarini, M ;
Di Giuseppe, S ;
Marinelli, F .
SYNLETT, 2003, (02) :203-206
[2]  
Balasubramanian M., 1996, COMPREHENSIVE HETERO, V5, P245, DOI 10.1016/B978-008096518-5.00109
[3]   Identification of xanthurenic acid as the putative inducer of malaria development in the mosquito [J].
Billker, O ;
Lindo, V ;
Panico, M ;
Etienne, AE ;
Paxton, T ;
Dell, A ;
Rogers, M ;
Sinden, RE ;
Morris, HR .
NATURE, 1998, 392 (6673) :289-292
[4]   MECHANISM OF FORMATION OF BENZO[G]QUINOLONES VIA COMBES REACTION [J].
BORN, JL .
JOURNAL OF ORGANIC CHEMISTRY, 1972, 37 (24) :3952-&
[5]   Preparation of 2′-aminoacetophenones:: a one-pot hydration and reduction of 1-ethynyl-2-nitrobenzenes [J].
Bosch, E ;
Jeffries, L .
TETRAHEDRON LETTERS, 2001, 42 (46) :8141-8142
[6]  
Buck J S, 1943, ORG SYNTH COLL VOL, V2, P130
[7]   One-pot three-component catalytic synthesis of fully substituted pyrroles from readily available propargylic alcohols, 1,3-dicarbonyl compounds and primary amines [J].
Cadierno, Victorio ;
Gimeno, Jose ;
Nebra, Noel .
CHEMISTRY-A EUROPEAN JOURNAL, 2007, 13 (35) :9973-9981
[8]   A novel propargylation/cycloisomerization tandem process catalyzed by a ruthenium(II)/trifluoroacetic acid system: One-pot entry to fully substituted furans from readily available secondary propargylic alcohols and 1,3-dicarbonyl compounds [J].
Cadierno, Victorio ;
Gimeno, Jose ;
Nebra, Noel .
ADVANCED SYNTHESIS & CATALYSIS, 2007, 349 (03) :382-394
[9]   Synthesis and antibacterial evaluation of certain quinolone derivatives [J].
Chen, YL ;
Fang, KC ;
Sheu, JY ;
Hsu, SL ;
Tzeng, CC .
JOURNAL OF MEDICINAL CHEMISTRY, 2001, 44 (14) :2374-2377
[10]   Ruthenium-catalyzed oxidative coupling and cyclization between 2-aminobenzyl alcohol and secondary alcohols leading to quinolines [J].
Cho, CS ;
Kim, BT ;
Choi, HJ ;
Kim, TJ ;
Shim, SC .
TETRAHEDRON, 2003, 59 (40) :7997-8002
1234567