Synthesis of 3-alkylideneisoindolinones and isoindolones by a Horner-Wadsworth-Emmons reaction

被引:16
作者
Angel Reyes-Gonzalez, Miguel [1 ]
Zamudio-Medina, Angel [1 ]
Abelardo Ramirez-Marroquin, Oscar [1 ]
Ordonez, Mario [1 ]
机构
[1] Univ Autonoma Estado Morelos, Ctr Invest Quim, Cuernavaca, Morelos, Mexico
来源
MONATSHEFTE FUR CHEMIE | 2014年 / 145卷 / 06期
关键词
Phosphonates; Three-component reaction; Wittig reaction; Heterocycles; ISOINDOLINONE DERIVATIVES; STEREOSELECTIVE-SYNTHESIS; EFFICIENT SYNTHESIS; INHIBITORY-ACTIVITY; POTENT INHIBITORS; CYCLIZATION; NITROGEN; ANALOG; LENNOXAMINE; DISCOVERY;
D O I
10.1007/s00706-013-1146-9
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
A series of 3-alkylideneisoindolinones was prepared by a Horner-Wadsworth-Emmons (HWE) reaction of aromatic aldehydes with N-(omega-hydroxyalkyl)substituted 3-phosphoisoindolin-1-ones, obtained in one-pot synthesis from 2-formylbenzoic acid. Additionally, the intramolecular HWE reaction of the N-(omega-formylalkyl)substituted phosphoisoindolin-1-ones afforded the corresponding isoindolone derivatives.
引用
收藏
页码:1001 / 1007
页数:7
相关论文
共 32 条
[1]   Practical and high stereoselective synthesis of 3-(arylmethylene)isoindolin-1-ones from 2-formylbenzoic acid [J].
Angel Reyes-Gonzalez, Miguel ;
Zamudio-Medina, Angel ;
Ordonez, Mario .
TETRAHEDRON LETTERS, 2012, 53 (43) :5756-5758
[2]   Product Selectivity Control in the Heteroannulation of o-(1-Alkynyl)benzamides [J].
Bianchi, Gabriele ;
Chiarini, Marco ;
Marinelli, Fabio ;
Rossi, Leucio ;
Arcadi, Antonio .
ADVANCED SYNTHESIS & CATALYSIS, 2010, 352 (01) :136-142
[3]  
Cappelli A, 2012, BIOORGAN MED CHEM, V10, P2681
[4]   Structure-activity relationships in a series of bisquaternary bisphthalimidine derivatives modulating the muscarinic M2-receptor allosterically [J].
Cid, HMB ;
Tränkle, C ;
Baumann, K ;
Pick, R ;
Mies-Klomfass, E ;
Kostenis, E ;
Mohr, K ;
Holzgrabe, U .
JOURNAL OF MEDICINAL CHEMISTRY, 2000, 43 (11) :2155-2164
[5]   An efficient one-pot synthesis of 3-(aryl and alkyl)methylene-1H-isoindolin-1-ones via aryne cyclization and Horner reaction of o- (and m-)halogeno-N-phosphorylmethylbenzamide derivatives. [J].
Couture, A ;
Deniau, E ;
Grandclaudon, P .
TETRAHEDRON, 1997, 53 (30) :10313-10330
[6]   Isoindolo[2,1-a]indol-6-one -: a new pyrolytic synthesis and some unexpected chemical properties [J].
Crawford, Lynne A. ;
Clemence, Nathan C. ;
McNab, Hamish ;
Tyas, Richard G. .
ORGANIC & BIOMOLECULAR CHEMISTRY, 2008, 6 (13) :2334-2339
[7]   A novel approach to isoindolo[2,1-a]indol-6-ones [J].
Duncanson, Philip ;
Cheong, Yuen-Ki ;
Motevalli, Majid ;
Griffiths, D. Vaughan .
ORGANIC & BIOMOLECULAR CHEMISTRY, 2012, 10 (21) :4266-4279
[8]   Discovery and SAR of substituted 3-oxoisoindoline-4-carboxamides as potent inhibitors of poly(ADP-ribose) polymerase (PARP) for the treatment of cancer [J].
Gandhi, Viraj B. ;
Luo, Yan ;
Liu, Xuesong ;
Shi, Yan ;
Klinghofer, Vered ;
Johnson, Eric F. ;
Park, Chang ;
Giranda, Vincent L. ;
Penning, Thomas D. ;
Zhu, Gui-Dong .
BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2010, 20 (03) :1023-1026
[9]   Synthesis of fused rings at a pivotal nitrogen:: tandem Heck reactions of N-vinyl-2-iodobenzamides [J].
García, A ;
Rodríguez, D ;
Castedo, L ;
Saá, C ;
Domínguez, D .
TETRAHEDRON LETTERS, 2001, 42 (10) :1903-1905
[10]  
Gourves JP, 1999, EUR J ORG CHEM, V1999, P3489, DOI 10.1002/(SICI)1099-0690(199912)1999:12<3489::AID-EJOC3489>3.0.CO