Synthesis of the functionalized spiro[indoline-3,5′-pyrroline]-2,2′-diones via three-component reactions of arylamines, acetylenedicarboxylates, and isatins

被引:58
作者
Han, Ying [1 ]
Wu, Qun [1 ]
Sun, Jing [1 ]
Yan, Chao-Guo [1 ]
机构
[1] Yangzhou Univ, Coll Chem & Chem Engn, Yangzhou 225002, Peoples R China
基金
中国国家自然科学基金;
关键词
Multicomponent reaction; Domino reaction; Electron-deficient alkyne; Isatin; Spiro compound; ONE-POT SYNTHESIS; EFFICIENT SYNTHESIS; MULTICOMPONENT REACTIONS; AROMATIC-ALDEHYDES; DIASTEREOSELECTIVE SYNTHESIS; 4-COMPONENT REACTIONS; AZOMETHINE YLIDES; FACILE SYNTHESIS; CONSTRUCTION; SPIRO;
D O I
10.1016/j.tet.2012.08.030
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
In the presence of p-toluenesulfonic acid as the catalyst the three-component reactions of arylamines, acetylenedicarboxylates, and isatins showed very interesting molecular diversity. When equal amount of arylamine was used, the three-component reaction resulted in the high yields of functionalized 3'-hydroxyspiro[indoline-3,5'-pyrroline]-2,2'-dione derivatives. On the other hand the functionalized 3'-N-arylaminospiro[indoline-3,5'-pyrroline]-2,2'-diones were also successfully prepared in satisfactory yields by using 2 M arylamine in the reaction. (C) 2012 Elsevier Ltd. All rights reserved.
引用
收藏
页码:8539 / 8544
页数:6
相关论文
共 44 条
[1]   Synthesis and evaluation of some new spiro indoline-based heterocycles as potentially active antimicrobial agents [J].
Abdel-Rahman, AH ;
Keshk, EM ;
Hanna, MA ;
El-Bady, SM .
BIOORGANIC & MEDICINAL CHEMISTRY, 2004, 12 (09) :2483-2488
[2]   A Novel, One-Pot Four-Component Route to 2′-Thioxo-2′,3′-dihydrospiro[indole-3,6′-[1,3]thiazin]-2-one Derivatives [J].
Alizadeh, Abdolali ;
Mokhtari, Javad .
HELVETICA CHIMICA ACTA, 2011, 94 (07) :1315-1319
[3]   A novel pseudo-seven-component diastereoselective synthesis of λ5-phosphanylidene bis(2,5-dioxotetrahydro-1H-pyrrole-3-carboxylates) via binucleophilic systems [J].
Alizadeh, Abdolali ;
Rostamnia, Sadegh ;
Zhu, Long-Guan .
TETRAHEDRON LETTERS, 2010, 51 (36) :4750-4754
[4]  
[Anonymous], 1996, CHEM INDOLES
[5]   Catalytic asymmetric synthesis of quaternary carbon centers.: Exploratory investigations of intramolecular Heck reactions of (E)-α,β-Unsaturated 2-haloanilides and analogues to form enantioenriched spirocyclic products [J].
Ashimori, A ;
Bachand, B ;
Overman, LE ;
Poon, DJ .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1998, 120 (26) :6477-6487
[6]   Titanium-Catalyzed Stereoselective Synthesis of Spirooxindole Oxazolines [J].
Badillo, Joseph J. ;
Arevalo, Gary E. ;
Fettinger, James C. ;
Franz, Annaliese K. .
ORGANIC LETTERS, 2011, 13 (03) :418-421
[7]   Simple and one-pot protocol for synthesis of indene-spiro-oxindoles involving tandem Prins and Friedel-Crafts reactions [J].
Basavaiah, Deevi ;
Reddy, Kanumuri Ramesh .
ORGANIC LETTERS, 2007, 9 (01) :56-60
[8]   An efficient synthesis of spiro[dibenzo[b,i]xanthene-13,3′-indoline]-pentaones and 5H-dibenzo[b,i]xanthene-tetraones [J].
Bazgir, Ayoob ;
Tisseh, Zeinab Noroozi ;
Mirzaei, Peiman .
TETRAHEDRON LETTERS, 2008, 49 (35) :5165-5168
[9]   Highly Enantioselective Construction of Spiro[4H-pyran-3,3′-oxindoles] Through a Domino Knoevenagel/Michael/Cyclization Sequence Catalyzed by Cupreine [J].
Chen, Wen-Bing ;
Wu, Zhi-Jun ;
Pei, Qing-Lan ;
Cun, Lin-Feng ;
Zhang, Xiao-Mei ;
Yuan, Wei-Cheng .
ORGANIC LETTERS, 2010, 12 (14) :3132-3135
[10]   Highly Regio- and Diastereoselective Construction of Spirocyclopenteneoxindoles through Phosphine-Catalyzed [3+2] Annulation of Morita-Baylis-Hillman Carbonates with Isatylidene Malononitriles [J].
Deng, Hong-Ping ;
Wei, Yin ;
Shi, Min .
ORGANIC LETTERS, 2011, 13 (13) :3348-3351