An efficient synthesis of 4,6-dihydrospiro[azepino[4,3,2-cd]indole-3,3′-indoline]-2′,5(1H)-diones via multi-component reaction

被引：17

作者：

Zou, Bin ^{[1
]}

Chen, Chun ^{[1
]}

Leong, Seh Yong ^{[1
]}

Ding, Mei ^{[1
]}

Smith, Paul W. ^{[1
]}

机构：

[1] Novartis Inst Trop Dis, Singapore 138670, Singapore

来源：

TETRAHEDRON | 2014年 / 70卷 / 03期

关键词：

Spiroazepinoindolone/spirooxindole; Isatin; Indolamine; Meldrum's acid; Multi-component reaction; ONE-POT SYNTHESIS; ENANTIOSELECTIVE SYNTHESIS; SPIROOXINDOLES; SPIROINDOLONES; HETEROCYCLES; DERIVATIVES; INHIBITORS; OXINDOLES; ISATINS; WATER;

D O I：

10.1016/j.tet.2013.12.010

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A facile and efficient one-pot three-component synthesis of spiroazepinoindolones has been developed. Using DMF as solvent without any additional acid or metal catalysts, the three-component reaction of readily available isatins, indolamines, and Meldrum's acid affords a new class of spiroheterocycles in moderate yield. (C) 2013 Published by Elsevier Ltd.

引用

收藏

页码：578 / 582

页数：5

相关论文

共 49 条

[1] Highly enantioselective synthesis and cellular evaluation of spirooxindoles inspired by natural products [J].

Antonchick, Andrey P. ;

Gerding-Reimers, Claas ;

Catarinella, Mario ;

Schuermann, Markus ;

Preut, Hans ;

Ziegler, Slava ;

Rauh, Daniel ;

Waldmann, Herbert .

NATURE CHEMISTRY, 2010, 2 (09) :735-740

[2] Synthesis of Novel Vicinal Coumarin- and Oxindole-Functionalized Dispiropyrrolidines and Dispiropyrrolizidines via [3+2]-Cycloaddition Reactions [J].

Bakthadoss, Manickam ;

Kannan, Damodharan ;

Sivakumar, Govindan .

SYNTHESIS-STUTTGART, 2012, 44 (05) :793-799

[3] New four-component reactions in water: a convergent approach to the metal-free synthesis of spiro[indoline/acenaphthylene-3,4′-pyrazolo[3,4-b]pyridine derivatives [J].

Balarnurugan, Kamaraj ;

Perumal, Subbu ;

Menendez, J. Carlos .

TETRAHEDRON, 2011, 67 (18) :3201-3208

[4] Strategies for the enantioselective synthesis of spirooxindoles [J].

Ball-Jones, Nicolas R. ;

Badillo, Joseph J. ;

Franz, Annaliese K. .

ORGANIC & BIOMOLECULAR CHEMISTRY, 2012, 10 (27) :5165-5181

[5]

BAN Y, 1974, TETRAHEDRON LETT, P187

[6] Synthesis of spiroindoline phytoalexin (S)-(-)-spirobrassinin and its unnatural (R)-(+)-enantiomer [J].

Budovska, Mariana ;

Kutschy, Peter ;

Kozar, Tibor ;

Gondova, Tatana ;

Petrovaj, Jan .

TETRAHEDRON, 2013, 69 (03) :1092-1104

[7] Efficient one-pot synthesis of spiro[indoline-3,4′-pyrazolo[3,4-e][1,4]thiazepine]dione via three-component reaction [J].

Chen, Hui ;

Shi, Daqing .

TETRAHEDRON, 2011, 67 (31) :5686-5692

[8] Organocatalytic Synthesis of Spiro[pyrrolidin-3,3′-oxindoles] with High Enantiopurity and Structural Diversity [J].

Chen, Xiao-Hua ;

Wei, Qiang ;

Luo, Shi-Wei ;

Xiao, Han ;

Gong, Liu-Zhu .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2009, 131 (38) :13819-13825

[9] Efficient microwave enhanced regioselective synthesis of a series of benzimidazolyl/triazolyl spiro [indole-thiazohdinones] as potent antifungal agents and crystal structure of spiro[3H-indole-3,2′-thiazolidine]-3′(1,2,4-triazol-3-yl)-2,4′(1H)-dione [J].

Dandia, A ;

Singh, R ;

Khaturia, S ;

Mérienne, C ;

Morgant, G ;

Loupy, A .

BIOORGANIC & MEDICINAL CHEMISTRY, 2006, 14 (07) :2409-2417

[10] New multicomponent domino reaction on water: highly diastereoselective synthesis of spiro[indoline-3,4′-pyrazolo[3,4-b]pyridines] catalyzed by NaCl [J].

Dandia, Anshu ;

Laxkar, Ashok Kumar ;

Singh, Ruby .

TETRAHEDRON LETTERS, 2012, 53 (24) :3012-3017

← 1 2 3 4 5 →