1,3-Dipolar Cycloaddition of Isatin-Derived Azomethine Ylides with 2H-Azirines: Stereoselective Synthesis of 1,3-Diazaspiro[bicyclo[3.1.0]hexane]oxindoles

被引：29

作者：

Angyal, Aniko ^{[1
,2
]}

Demjen, Andras ^{[1
]}

Harmat, Veronika ^{[3
,4
]}

Wolfling, Janos ^{[2
]}

Puskas, Laszlo G. ^{[1
]}

Kanizsai, Ivan ^{[1
]}

机构：

[1] AVIDIN Ltd, Also Kikoto Sor 11-D, H-6726 Szeged, Hungary

[2] Univ Szeged, Dept Organ Chem, Dom Ter 8, H-6720 Szeged, Hungary

[3] Eotvos Lorand Univ, Lab Struct Chem & Biol, Inst Chem, Pazmany P Setany 1-A, H-1117 Budapest, Hungary

[4] Eotvos Lorand Univ, MTA ELTE Prot Modeling Res Grp, Inst Chem, Pazmany P Setany 1-A, H-1117 Budapest, Hungary

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2019年 / 84卷 / 07期

关键词：

FUSED SPIROPYRROLIDINE OXINDOLES; ENANTIOSELECTIVE CONSTRUCTION; AQUEOUS-MEDIUM; PYRROLIDINE; DIVERSITY; DERIVATIVES; POTENT; IMIDAZOLIDINES; CYCLIZATION; DISCOVERY;

D O I：

10.1021/acs.joc.9b00242

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A regio- and diastereoselective 1,3-dipolar cycloaddition of 2H-azirines with azomethine ylides generated in situ from isatins and alpha-amino acids has been elaborated, affording an unprecedented aziridine-fused spiro[imidazolidine-4,3'-oxindole] framework. This one-pot three-component reaction tolerates a wide range of substrates and enables the construction of highly diverse 1,3-diazaspiro[bicyclo[3.1.0]hexane]oxindoles in isolated yields up to 81% under mild conditions.

引用

页码：4273 / 4281

页数：9

共 53 条

[1] Organocatalyzed nucleophilic addition of pyrazoles to 2H-azirines: asymmetric synthesis of 3,3-disubstituted aziridines and kinetic resolution of racemic 2H-azirines [J].

An, Dong ;

Guan, Xukai ;

Guan, Rui ;

Jin, Lajiao ;

Zhang, Guangliang ;

Zhang, Suoqin .

CHEMICAL COMMUNICATIONS, 2016, 52 (75) :11211-11214

[2] Lewis Acid-Catalyzed Diastereoselective Synthesis of Multisubstituted N-Acylaziridine-2-carboxamides from 2H-Azirines via Joullie-Ugi Three-Component Reaction [J].

Angyal, Aniko ;

Demjen, Andras ;

Weber, Edit ;

Kovacs, Anita K. ;

Wolfling, Janos ;

Puskas, Laszlo G. ;

Kanizsai, Ivan .

JOURNAL OF ORGANIC CHEMISTRY, 2018, 83 (07) :3570-3581

[3] Regio- and stereoselective 1,3-dipolar cycloaddition of indenoquinoxalinone azomethine ylides to β-nitrostyrenes: synthesis of spiro[indeno[1,2-b]quinoxaline-11,3′-pyrrolizidines] and spiro[indeno[1,2-b]quinoxaline-11,2′-pyrrolidines] [J].

Barkov, Aleksey Yi. ;

Zimnitskiy, Nikolay S. ;

Korotaev, Vladislav Yu. ;

Kutyashev, Igor B. ;

Moshkin, Vladimir S. ;

Sosnovskikh, Vyacheslav Ya. .

CHEMISTRY OF HETEROCYCLIC COMPOUNDS, 2017, 53 (04) :451-459

[4] Synthesis of Spirocyclic Pyrrolidines: Advanced Building Blocks for Drug Discovery [J].

Chalyk, Bohdan A. ;

Butko, Maryna V. ;

Yanshyna, Oksana O. ;

Gavrilenko, Konstantin S. ;

Druzhenko, Tetiana V. ;

Mykhailiuk, Pavel K. .

CHEMISTRY-A EUROPEAN JOURNAL, 2017, 23 (66) :16782-16786

[5] Advances in matrix metalloproteinase inhibitors based on pyrrolidine scaffold [J].

Cheng, Xian-Chao ;

Wang, Qiang ;

Fang, Hao ;

Xu, Wen-Fang .

CURRENT MEDICINAL CHEMISTRY, 2008, 15 (04) :374-385

[6] Discovery of a new class of potent, selective, and orally bioavailable CRTH2 (DP2) receptor antagonists for the treatment of allergic inflammatory diseases [J].

Crosignani, Stefano ;

Page, Patrick ;

Missotten, Marc ;

Colovray, Veronique ;

Cleva, Christophe ;

Arrighi, Jean-Francois ;

Atherall, John ;

Macritchie, Jackie ;

Martin, Thierry ;

Humbert, Yves ;

Gaudet, Marilene ;

Pupowicz, Doris ;

Maio, Maurizio ;

Pittet, Pierre-Andre ;

Golzio, Lucia ;

Giachetti, Claudio ;

Rocha, Cynthia ;

Bernardinelli, Gerald ;

Filinchuk, Yaroslav ;

Scheer, Alexander ;

Schwarz, Matthias K. ;

Chollet, Andre .

JOURNAL OF MEDICINAL CHEMISTRY, 2008, 51 (07) :2227-2243

[7] Diastereo- and Enantioselective Construction of 3,3′-Pyrrolidinyldispirooxindole Framework via Catalytic Asymmetric 1,3-Dipolar Cycloadditions [J].

Dai, Wei ;

Jiang, Xiao-Li ;

Wu, Qiong ;

Shi, Feng ;

Tu, Shu-Jiang .

JOURNAL OF ORGANIC CHEMISTRY, 2015, 80 (11) :5737-5744

[8] Diastereo- and Enantioselective Construction of a Bispirooxindole Scaffold Containing a Tetrahydro-β-carboline Moiety through an Organocatalytic Asymmetric Cascade Reaction [J].

Dai, Wei ;

Lu, Han ;

Li, Xin ;

Shi, Feng ;

Tu, Shu-Jiang .

CHEMISTRY-A EUROPEAN JOURNAL, 2014, 20 (36) :11382-11389

[9] Structure-based design of potent non-peptide MDM2 inhibitors [J].

Ding, K ;

Lu, Y ;

Nikolovska-Coleska, Z ;

Qiu, S ;

Ding, YS ;

Gao, W ;

Stuckey, J ;

Krajewski, K ;

Roller, PP ;

Tomita, Y ;

Parrish, DA ;

Deschamps, JR ;

Wang, SM .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2005, 127 (29) :10130-10131

[10] Total synthesis of spirotryprostatin A, leading to the discovery of some biologically promising analogues [J].

Edmondson, S ;

Danishefsky, SJ ;

Sepp-Lorenzino, L ;

Rosen, N .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1999, 121 (10) :2147-2155

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