Synthesis of Aryl Substituted Quinones as β-Secretase Inhibitors: Ligand-Free Direct Arylation of Quinones with Aryl Halides

被引:9
作者
Wang, Dawei [1 ]
Ge, Bingyang [1 ]
Yang, Shuyan [1 ]
Miao, Hongyan [1 ]
Ding, Yuqiang [1 ]
机构
[1] Jiangnan Univ, Sch Chem & Mat Engn, Key Lab Food Colloids & Biotechnol, Minist Educ, Wuxi 214122, Jiangsu, Peoples R China
基金
中国国家自然科学基金;
关键词
ligand-free; quinones; inhibitors; arylation; Heck reaction; CONJUGATE ADDITION; ARYLBORONIC ACIDS; NAPHTHOQUINONES; BIOSYNTHESIS; ARYLQUINONES; ACTIVATION; DISCOVERY; OXIDATION; INDOLES; WATER;
D O I
10.1134/S1070363214080295
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
The simple ligand-free direct arylation of quinones with aryl halides applying Pd(OAc)(2) as a catalyst in accordance with Heck reaction was studied. This reaction provided a simple and efficient synthetic approach to efficient inhibitors of beta-secretase aryl-substituted quinones.
引用
收藏
页码:1615 / 1621
页数:7
相关论文
共 41 条
[1]  
Babula P, 2006, Ceska Slov Farm, V55, P151
[2]  
Babula P, 2007, Ceska Slov Farm, V56, P114
[3]   The heck reaction as a sharpening stone of palladium catalysis [J].
Beletskaya, IP ;
Cheprakov, AV .
CHEMICAL REVIEWS, 2000, 100 (08) :3009-3066
[4]   The core and most useful molecules in organic chemistry [J].
Bishop, Kyle J. M. ;
Klajn, Rafal ;
Grzybowski, Bartosz A. .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2006, 45 (32) :5348-5354
[5]   Strategies for disease modification in Alzheimer's disease [J].
Citron, M .
NATURE REVIEWS NEUROSCIENCE, 2004, 5 (09) :677-685
[6]   Mitomycin synthetic studies: Stereocontrolled and convergent synthesis of a fully elaborated aziridinomitosane [J].
Coleman, RS ;
Felpin, FX ;
Chen, W .
JOURNAL OF ORGANIC CHEMISTRY, 2004, 69 (21) :7309-7316
[7]   Iron-Catalyzed Direct C-H Arylation of Heterocycles and Quinones with Arylboronic Acids [J].
Deb, Arghya ;
Manna, Srimanta ;
Maji, Arun ;
Dutta, Uttam ;
Maiti, Debabrata .
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2013, 2013 (24) :5251-5256
[8]   New and Efficient Protocol for Arylation of Quinones [J].
Demchuk, Oleg M. ;
Pietrusiewicz, K. Michal .
SYNLETT, 2009, (07) :1149-1153
[9]   The role of amyloid β peptide 42 in Alzheimer's disease [J].
Findeis, Mark A. .
PHARMACOLOGY & THERAPEUTICS, 2007, 116 (02) :266-286
[10]   Practical C-H Functionalization of Quinones with Boronic Acids [J].
Fujiwara, Yuta ;
Domingo, Victoriano ;
Seiple, Ian B. ;
Gianatassio, Ryan ;
Del Bel, Matthew ;
Baran, Phil S. .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2011, 133 (10) :3292-3295