Reductive coupling of aliphatic cyclic imides with benzophenones by low-valent titanium

被引:7
作者
Kise, Naoki [1 ]
Kinameri, Syn [1 ]
Sakurai, Toshihiko [1 ]
机构
[1] Tottori Univ, Dept Chem & Biotechnol, Grad Sch Engn, Minami Ku, Tottori 6808552, Japan
关键词
Reductive coupling; Low-valent titanium; McMurry coupling; Aliphatic cyclic imides; Benzophenones; ESTROGEN-RECEPTOR MODULATORS; KETONES; LACTAMS;
D O I
10.1016/j.tetlet.2013.10.053
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The reductive coupling of aliphatic cyclic imides with benzophenones by Zn-TiCl4 in THF gave two- and four-electron reduced products selectively by controlling the reaction conditions. Although cyclic and acyclic products were formed as mixtures in most cases, cyclic dehydrated products could be selectively obtained by heating the product mixtures in the presence of cat. p-TsOH. (C) 2013 Elsevier Ltd. All rights reserved.
引用
收藏
页码:6944 / 6948
页数:5
相关论文
共 14 条
[1]   REACTION OF N-BENZYLPYROGLUTAMIC ACID WITH PHENYL GRIGNARD [J].
CAMPAIGNE, E ;
MATTHEWS, DP .
JOURNAL OF HETEROCYCLIC CHEMISTRY, 1975, 12 (02) :391-392
[2]   Facile two-step synthesis of 2-arylbenzofurans based on the selective cross McMurry couplings [J].
Duan, Xin-Fang ;
Zeng, Jing ;
Zhang, Zhan-Bin ;
Zi, Guo-Fu .
JOURNAL OF ORGANIC CHEMISTRY, 2007, 72 (26) :10283-10286
[3]   Insights into the general and efficient cross McMurry reactions between ketones [J].
Duan, Xin-Fang ;
Zeng, Jing ;
Lu, Jia-Wei ;
Zhang, Zhan-Bin .
JOURNAL OF ORGANIC CHEMISTRY, 2006, 71 (26) :9873-9876
[4]  
Frisch M, 2015, Gaussian 09, revision a 02
[5]   New developments in the chemistry of low-valent titanium [J].
Furstner, A ;
Bogdanovic, B .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1996, 35 (21) :2442-2469
[6]   PHOTO-REDUCTION OF ARYL KETONES BY AMIDES AND LACTAMS - SYNTHETIC APPLICATION [J].
GRAMAIN, JC ;
REMUSON, R ;
TROIN, Y .
TETRAHEDRON, 1979, 35 (06) :753-758
[7]   Reductive coupling of N-methoxycarbonyl lactams with benzophenone and 9-fluorenone by low-valent titanium [J].
Kise, Naoki ;
Takenaga, Yosei ;
Ishikawa, Yohei ;
Morikami, Yoichi ;
Sakurai, Toshihiko .
TETRAHEDRON LETTERS, 2012, 53 (15) :1940-1945
[8]   Reductive coupling of 1,3-dimethyluracils with benzophenone by low-valent titanium: unusual two-to-one coupling [J].
Kise, Naoki ;
Akazai, Shinta ;
Sakurai, Toshihiko .
TETRAHEDRON LETTERS, 2011, 52 (49) :6627-6631
[9]   CARBONYL-COUPLING REACTIONS USING LOW-VALENT TITANIUM [J].
MCMURRY, JE .
CHEMICAL REVIEWS, 1989, 89 (07) :1513-1524
[10]   Selective estrogen receptor modulators in the ruthenocene series.: Synthesis and biological behavior [J].
Pigeon, P ;
Top, S ;
Vessières, A ;
Huché, M ;
Hillard, EA ;
Salomon, E ;
Jaouen, G .
JOURNAL OF MEDICINAL CHEMISTRY, 2005, 48 (08) :2814-2821