Reductive Heck Reactions and [3+2] Cycloadditions of Unsaturated N,N'-Bistricyclic Imides

被引:0
作者
Gul, Melek [2 ]
Kulu, Irem [1 ]
Gunkara, Omer Tahir [1 ]
Ocal, Nuket [1 ]
机构
[1] Yildiz Tech Univ, Fac Sci & Arts, TR-34220 Esenler, Turkey
[2] Univ Amasya, Fac Sci & Arts, TR-05100 Amasya, Turkey
关键词
Alkenes; cycloadditions; heterocycles; hydroarylations; triyclic imides; SUBSTITUTED CYCLIC IMIDES; HYDROARYLATION; EPIBOXIDINE; ANALOGS; DICARBOXIMIDES; ANTICANCER;
D O I
暂无
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
The C-C coupling of N,N'-bis(5-norbornene-2,3-dicarboximide) (3) and N,N'-bis(7-oxa-5-norbornene-2,3-dicarboximide) (6) with aryl and heteroaryl iodides gave under reductive Heck conditions the C-aryl(hetaryl), substituted N,N'bistricyclic imides 7a-f and 8a,b. The fused spiro-1,3-indandionolylpyrrolidine compounds, 9, 10 and 11 were also obtained from ninhydrine, sarcosine and 3 or 6 via [3+2] cycloaddition.
引用
收藏
页码:87 / 94
页数:8
相关论文
共 29 条
[1]   Synthesis and nicotinic activity of epiboxidine: An isoxazole analogue of epibatidine [J].
Badio, B ;
Garraffo, HM ;
Plummer, CV ;
Padgett, WL ;
Daly, JW .
EUROPEAN JOURNAL OF PHARMACOLOGY, 1997, 321 (02) :189-194
[2]   An investigation into domino-Heck reactions of N-acylamino-substituted tricyclic imides:: Synthesis of new prospective pharmaceuticals [J].
Bagdatli, Emine ;
Ocal, Nueket ;
Kaufmann, Dieter E. .
HELVETICA CHIMICA ACTA, 2007, 90 (12) :2380-2385
[3]   The heck reaction as a sharpening stone of palladium catalysis [J].
Beletskaya, IP ;
Cheprakov, AV .
CHEMICAL REVIEWS, 2000, 100 (08) :3009-3066
[4]   Domino-Heck Reactions of Carba- and Oxabicyclic, Unsaturated Dicarboximides: Synthesis of Aryl-Substituted, Bridged Perhydroisoindole Derivatives [J].
Celik, Cumali ;
Kulu, Irem ;
Ocal, Nuket ;
Kaufmann, Dieter E. .
HELVETICA CHIMICA ACTA, 2009, 92 (06) :1092-1101
[5]   THE SYNTHESIS OF 2-AZA-1,2-DIHYDRODICYCLOPENTADIENES [J].
CULBERSON, CF ;
WILDER, P .
JOURNAL OF ORGANIC CHEMISTRY, 1960, 25 (08) :1358-1362
[6]   Cyclic imides as potent and selective α-1A adrenergic receptor antagonists [J].
DiPardo, RM ;
Patane, MA ;
Newton, RC ;
Price, RA ;
Broten, TP ;
Chang, RSL ;
Ransom, RW ;
Di Salvo, J ;
Freidinger, RM ;
Bock, MG .
BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2001, 11 (14) :1959-1962
[7]   Hydroarylation of bicyclic, unsaturated dicarboximides:: access to aryl-substituted, bridged perhydroisoindoles [J].
Goeksu, Goekce ;
Guel, Melek ;
Oecal, Nueket ;
Kaufmann, Dieter E. .
TETRAHEDRON LETTERS, 2008, 49 (17) :2685-2688
[8]  
Goksu G, 2011, ACTA CHIM SLOV, V58, P256
[9]   Reductive Heck Reactions of N-Methyl-substituted Tricyclic Imides [J].
Goksu, Gokce ;
Ocal, Nuket ;
Kaufmann, Dieter E. .
MOLECULES, 2010, 15 (03) :1302-1308
[10]   PREPARATION AND PROPERTIES OF SOME NEW N,N'-BIISOIMIDES AND THEIR CYCLIC ISOMERS . REACTION OF N,N'-BIISOMALEIMIDE WITH DIENES [J].
HEDAYA, E ;
HINMAN, RL ;
THEODORO.S .
JOURNAL OF ORGANIC CHEMISTRY, 1966, 31 (05) :1317-&