An Efficient Protocol for Multicomponent Synthesis of Spirooxindoles Employing L-Proline as Catalyst at Room Temperature

被引：37
作者：
Raghuvanshi, Dushyant Singh [1 ]
Singh, Krishna Nand [1 ]
机构：
[1] Banaras Hindu Univ, Fac Sci, Dept Chem, Varanasi 221005, Uttar Pradesh, India
来源：
JOURNAL OF HETEROCYCLIC CHEMISTRY | 2010年 / 47卷 / 06期
关键词：
MAMMALIAN-CELL CYCLE; ASYMMETRIC-SYNTHESIS; DERIVATIVES; ISATINS; CHEMISTRY; FACILE; SPIROTRYPROSTATIN; MALONONITRILE; COMBINATORIAL; INHIBITORS;
D O I：
10.1002/jhet.451
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
An efficient three-component one-pot synthesis of medicinally important spirooxindoles is described by the reaction of isatin, malononitrile/ethyl cyanoacetate, and dimedone/barbituric acid using L-proline as catalyst in ethanol at room temperature. This approach is convenient, mild, and affords the products in high yields without the use of chromatography.
引用
收藏
页码：1323 / 1327
页数：5
相关论文
共 72 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]   Efficient entry to diversely functionalized spirocyclic oxindoles from isatins through carbonyl-addition/cyclization reaction sequences [J].
Alcaide, B ;
Almendros, P ;
Rodríguez-Acebes, R .
JOURNAL OF ORGANIC CHEMISTRY, 2006, 71 (06) :2346-2351
[3]  
Alper PB, 1999, ANGEW CHEM INT EDIT, V38, P3186, DOI 10.1002/(SICI)1521-3773(19991102)38:21<3186::AID-ANIE3186>3.0.CO
[4]  
2-E
[5]   Aminocyanopyridine inhibitors of mitogen activated protein kinase-activated protein kinase 2 (MK-2) [J].
Anderson, DR ;
Hegde, S ;
Reinhard, E ;
Gomez, L ;
Vernier, WF ;
Lee, L ;
Liu, S ;
Sambandam, A ;
Snider, PA ;
Masih, L .
BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2005, 15 (06) :1587-1590
[6]  
[Anonymous], 1997, COUMARINS BIOL APPL
[7]   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
[8]   Organocatalytic regio- and asymmetric C-selective SNAr reactions-stereoselective synthesis of optically active spiro-pyrrolidone-3,3′-oxoindoles [J].
Bella, M ;
Kobbelgaard, S ;
Jorgensen, KA .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2005, 127 (11) :3670-3671
[9]   Simple coumarins and analogues in medicinal chemistry: Occurrence, synthesis and biological activity [J].
Borges, F ;
Roleira, F ;
Milhazes, N ;
Santana, L ;
Uriarte, E .
CURRENT MEDICINAL CHEMISTRY, 2005, 12 (08) :887-916
[10]   Convergent diversity-oriented synthesis of small-molecule hybrids [J].
Chen, C ;
Li, XD ;
Neumann, CS ;
Lo, MMC ;
Schreiber, SL .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2005, 44 (15) :2249-2252
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