Introduction of ethynylene and thienylene spacers into 2,5-diarylthiazole and 2,5-diarylthiophene

被引:46
作者
Kobayashi, Kei [1 ]
Ahmed, Mohamed S. Mohamed [1 ]
Mori, Atsunori [1 ]
机构
[1] Tokyo Inst Technol, Chem Resources Lab, Yokohama, Kanagawa 2268503, Japan
关键词
sonogashira coupling; 2-ethanolamine; palladium catalyst; CH arylation;
D O I
10.1016/j.tet.2006.07.097
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Syntheses of 2,5-diarylthiazole and 2,5-diarylthiophene derivatives bearing ethynylene and thienylene spacers are performed. With the methods for coupling reactions of terminal alkynes and at the CH bond of heteroaromatic compounds, which we have developed, five kinds of thiazole and thiophene derivatives 3-7 are prepared. Spectroscopic characteristics of 3-7 are also measured. (c) 2006 Elsevier Ltd. All rights reserved.
引用
收藏
页码:9548 / 9553
页数:6
相关论文
共 59 条
[1]   One-pot construction of pyrazoles and isoxazoles with palladium-catalyzed four-component coupling [J].
Ahmed, MSM ;
Kobayashi, K ;
Mori, A .
ORGANIC LETTERS, 2005, 7 (20) :4487-4489
[2]  
Ahmed MSM, 2005, B CHEM SOC JPN, V78, P160
[3]   New activators for the coupling reaction of terminal alkynes with organic halides [J].
Ahmed, MSM ;
Sekiguchi, A ;
Shimada, T ;
Kawashima, J ;
Mori, A .
BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN, 2005, 78 (02) :327-330
[4]   Sonogashira coupling with aqueous ammonia directed to the synthesis of azotolane derivatives [J].
Ahmed, MSM ;
Mori, A .
TETRAHEDRON, 2004, 60 (44) :9977-9982
[5]   Carbonylative Sonogashira coupling of terminal alkynes with aqueous ammonia [J].
Ahmed, MSM ;
Mori, A .
ORGANIC LETTERS, 2003, 5 (17) :3057-3060
[6]   AN EFFICIENT PALLADIUM-CATALYZED REACTION OF VINYL AND ARYL HALIDES OR TRIFLATES WITH TERMINAL ALKYNES [J].
ALAMI, M ;
FERRI, F ;
LINSTRUMELLE, G .
TETRAHEDRON LETTERS, 1993, 34 (40) :6403-6406
[7]   Use of the extended one-pot (EOP) procedure for the preparation of ethynylated thiophene derivatives and related palladium-ethynylthiophene organometallic oligomers [J].
Altamura, P ;
Giardina, G ;
Lo Sterzo, C ;
Russo, MV .
ORGANOMETALLICS, 2001, 20 (21) :4360-4368
[8]   NEW SYNTHETIC APPLICATIONS OF WATER-SOLUBLE ACETATE PD/TPPTS CATALYST GENERATED IN-SITU - EVIDENCE FOR A TRUE PD(0) SPECIES INTERMEDIATE [J].
AMATORE, C ;
BLART, E ;
GENET, JP ;
JUTAND, A ;
LEMAIREAUDOIRE, S ;
SAVIGNAC, M .
JOURNAL OF ORGANIC CHEMISTRY, 1995, 60 (21) :6829-6839
[9]  
[Anonymous], METAL CATALYZED CROS
[10]  
Briehn CA, 2001, ANGEW CHEM INT EDIT, V40, P4680, DOI 10.1002/1521-3773(20011217)40:24<4680::AID-ANIE4680>3.0.CO