Indium(III) halides-catalyzed preparation of ferrocene-dihydropyrimidinones

被引:61
作者
Fu, NY
Yuan, YF
Pang, ML
Wang, JT
Peppe, C [1 ]
机构
[1] Univ Fed Santa Maria, Dept Quim, Lab Mat Inorgan, BR-97105900 Santa Maria, RS, Brazil
[2] Nankai Univ, Dept Chem, State Key Lab Elementoorgan Chem, Tianjin 300071, Peoples R China
基金
中国国家自然科学基金;
关键词
indium(III) halides; biginelli coupling; ferrocene-dihydropyrimidinones;
D O I
10.1016/S0022-328X(03)00139-6
中图分类号
O61 [无机化学];
学科分类号
070301 ; 081704 ;
摘要
Indium(III) halides (chloride and bromide) catalyse the three-component Biginelli coupling of ferrocenyl-1,3-diketones, aldehydes and urea (or thiourea) to give 5-ferrocenoyl-3,4-dihydropyrimidinones. 4-Ferrocenyl-3,4-dihydropyrimidinones were obtained from alkyl-acetoacetates, formylferrocene and urea. The tricyclic compound, 13-ferrocenecarbonyl-9-methyl-11-oxo-8-oxa-10,12-diazatricyclo [7.3.1.0(2.7)] trideca-2,4-6-triene, was synthesized from 1-ferrocenyl-1,3-butanedione, salicilaldehyde and urea. (C) 2003 Elsevier Science B.V. All rights reserved.
引用
收藏
页码:52 / 57
页数:6
相关论文
共 22 条
[1]  
AI G, 1998, SYN REACT INORG MET, V28, P811
[2]  
Biginelli P., 1893, GAZZ CHIM ITAL, V23, P360
[3]   Novel ferrocenic artemisinin derivatives: Synthesis, in vitro antimalarial activity and affinity of binding with ferroprotoporphyrin IX [J].
Delhaes, L ;
Biot, C ;
Berry, L ;
Maciejewski, LA ;
Camus, D ;
Brocard, JS ;
Dive, D .
BIOORGANIC & MEDICINAL CHEMISTRY, 2000, 8 (12) :2739-2745
[4]   Synthesis of ferrocene substituted pyrrolidine derivatives via Et2Zn catalyzed 1,3-dipolar cycloaddition reactions of azomethine ylides [J].
Dogan, Ö ;
Koyuncu, H .
JOURNAL OF ORGANOMETALLIC CHEMISTRY, 2001, 631 (1-2) :135-138
[5]   Cyclic voltammetry of ferrocene-containing β-diketones as a tool to obtain group electronegativities.: The structure of 3-ferrocenoyl-1,1,1-trifluoro-2-hydroxyprop-2-ene [J].
du Plessis, WC ;
Erasmus, JJC ;
Lamprecht, GJ ;
Conradie, J ;
Cameron, TS ;
Aquino, MAS ;
Swarts, JC .
CANADIAN JOURNAL OF CHEMISTRY-REVUE CANADIENNE DE CHIMIE, 1999, 77 (03) :378-386
[6]   Indium(III) bromide-catalyzed preparation of dihydropyrimidinones: improved protocol conditions for the Biginelli reaction [J].
Fu, NY ;
Yuan, YF ;
Cao, Z ;
Wang, SW ;
Wang, JT ;
Peppe, C .
TETRAHEDRON, 2002, 58 (24) :4801-4807
[7]   Synthesis, structure and coordination chemistry of mono- and bis-heterocyclic-ferrocenyl derivatives [J].
Isaac, CJ ;
Price, C ;
Horrocks, BR ;
Houlton, A ;
Elsegood, MRJ ;
Clegg, W .
JOURNAL OF ORGANOMETALLIC CHEMISTRY, 2000, 598 (02) :248-253
[8]   Recent advances in the Biginelli dihydropyrimidine synthesis. New tricks from an old dog [J].
Kappe, CO .
ACCOUNTS OF CHEMICAL RESEARCH, 2000, 33 (12) :879-888
[9]   The reactions of semicarbazide and thiosemicarbazide with ferrocenyl-substituted α,β-enones [J].
Klimova, T ;
Klimova, EI ;
García, MM ;
Stivalet, JMM ;
Ramírez, LR .
JOURNAL OF ORGANOMETALLIC CHEMISTRY, 2001, 633 (1-2) :137-142
[10]  
KORRIYOUSSOUFI H, 2001, SYNTHETIC MET, V66, P2937