Palladium-catalyzed direct arylation of maleimides: A simple route to bisaryl-substituted maleimides

被引:17
作者
Jafarpour, Farnaz [1 ]
Shamsianpour, Mitra [1 ]
Issazadeh, Salumeh [1 ]
Dorrani, Masoumeh [1 ]
Hazrati, Hamideh [1 ]
机构
[1] Univ Tehran, Coll Sci, Sch Chem, P Box 14155-6455, Tehran, Iran
关键词
Boronic acids; Direct arylation; Maleimide; Oxidative Heck reaction; Palladium; LIGHT-EMITTING-DIODES; BIOLOGICAL EVALUATION; CONVENIENT SYNTHESIS; EFFICIENT SYNTHESIS; 3,4-DIARYLMALEIMIDES; FLUORESCENCE; DOCKING; ALKYNES; POTENT;
D O I
10.1016/j.tet.2017.01.069
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Palladium-catalyzed direct arylation of maleimides via Heck as well as organoboron-mediated Heck-type reactions are developed. These methods offer an approach to a wide variety of biologically interesting 3,4-diarylmaleimide scaffolds from readily accessible starting materials. These approaches led to the feasible one-pot construction of bisaryl-substituted maleimides which have historically been problematic. (C) 2017 Published by Elsevier Ltd.
引用
收藏
页码:1668 / 1672
页数:5
相关论文
共 33 条
[1]   Development of Methods for the Synthesis of Libraries of Substituted Maleimides and α,β-Unsaturated-γ-butyrolactams [J].
Awuah, Emelia ;
Capretta, Alfredo .
JOURNAL OF ORGANIC CHEMISTRY, 2011, 76 (09) :3122-3130
[2]   Coupling reactions of indole-3-acetic acid derivatives. Synthesis of arcyriaflavin A [J].
Bergman, J ;
Koch, E ;
Pelcman, B .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 2000, (16) :2609-2614
[3]   Structure-Activity Relationship Study of Permethyl Ningalin B Analogues as P-Glycoprotein Chemosensitizers [J].
Bin, Jin Wen ;
Wong, Iris L. K. ;
Hu, Xuesen ;
Yu, Zhang Xiao ;
Xing, Li Fu ;
Jiang, Tao ;
Chow, Larry M. C. ;
Biao, Wan Sheng .
JOURNAL OF MEDICINAL CHEMISTRY, 2013, 56 (22) :9057-9070
[4]   Helicenes from Diarylmaleimides [J].
Bock, Harald ;
Subervie, Daniel ;
Mathey, Pierre ;
Pradhan, Anirban ;
Sarkar, Parantap ;
Dechambenoit, Pierre ;
Hillard, Elizabeth A. ;
Durola, Fabien .
ORGANIC LETTERS, 2014, 16 (06) :1546-1549
[5]   Synthesis of 3,4-Disubstituted Maleimides by Selective Cross-Coupling Reactions Using Indium Organometallics [J].
Bouissane, Latifa ;
Perez Sestelo, Jose ;
Sarandeses, Luis A. .
ORGANIC LETTERS, 2009, 11 (06) :1285-1288
[6]   The Spermine-Bisaryl Conjugate as a Potent Inducer of B- to Z-DNA Transition [J].
Doi, Issei ;
Tsuji, Genichiro ;
Kawakami, Kyoko ;
Nakagawa, Osamu ;
Taniguchi, Yosuke ;
Sasaki, Shigeki .
CHEMISTRY-A EUROPEAN JOURNAL, 2010, 16 (39) :11993-11999
[7]   Convenient synthesis of photochromic symmetrical or unsymmetrical bis(heteroaryl)maleimides via the Suzuki-Miyaura cross-coupling reaction [J].
El Yahyaoui, A. ;
Felix, G. ;
Heynderickx, A. ;
Moustrou, C. ;
Samat, A. .
TETRAHEDRON, 2007, 63 (38) :9482-9487
[8]   A new one step synthesis of maleimides by condensation of glyoxylate esters with acetamides [J].
Faul, MM ;
Winneroski, LL ;
Krumrich, CA .
TETRAHEDRON LETTERS, 1999, 40 (06) :1109-1112
[9]   A new, efficient method for the synthesis of bisindolylmaleimides [J].
Faul, MM ;
Winneroski, LL ;
Krumrich, CA .
JOURNAL OF ORGANIC CHEMISTRY, 1998, 63 (17) :6053-6058
[10]   Total synthesis of didemnimide A and B [J].
Hughes, TV ;
Cava, MP .
TETRAHEDRON LETTERS, 1998, 39 (52) :9629-9630