Synthesis of Fluorinated Isoquinoline-1,3-Dione via Light-Catalysis Addition and Cyclization of Alkenes

doi:10.3969/j.cnki.jdxb.2017.03.014

Abstract

Abstract:

A synthesis of fluorinated isoquinoline-1,3-diones via light catalyzing activated alkenes addition reaction was developed.Through light catalysis,various N-alkyl-N-methacryloylbenamides derivatives underwent radical cascade addition cyclization reaction with perfluorobutyliodide and ethyl bromodifluoroacetate.A series of fluorinated isoquinoline-1,3-diones derivatives with potential physiological activity was compounded in 67%~80% yields.This study provides a green efficient approach to afford fluorinated isoquinoline-1,3-dione under mild conditions.

Key words: light catalysis, C&mdash, H cyclization, free radical, fluorinated isoquinoline-1,3-dione

ZHANG Qian,WANG Qiong,DENG Youlin,WANG Shuowen,YUAN Li,WU Yiting,TANG Shi. Synthesis of Fluorinated Isoquinoline-1,3-Dione via Light-Catalysis Addition and Cyclization of Alkenes[J]. Journal of Jishou University（Natural Sciences Edition), DOI: 10.3969/j.cnki.jdxb.2017.03.014.

References

[1] PRAKASH G S,CHACKO S.Novel Nucleophilic and Electrophilic Fluoroalkylation Methods[J].Current Opinion in Drug Discovery and Development,2008,11(6):793-802.
[2] 唐裕,张敏,李小青,等.四丁基碘化胺催化活化烯烃烷氧羰基化反应:合成异喹啉二酮衍生物[J].有机化学,2015(4):875-881.
[3] CHEN Yihua,ZHANG Yahui,ZHANG Huajie,et al.Design,Synthesis,and Biological Evaluation of Isoqui-noline-1,3,4-Trione Derivatives as Potent Caspase-3 Inhibitors[J].Journal of Medicinal Chemistry,2006,49(5):1 613-1 623.
[4] BRA〖AKN~〗A M F,CASTELLANO J M,PERRON D,et al.Chromophore-Modified Bis-Naphthali Mides:Synthesis and Antitumor Activity of Bis-Dibenz[de,h]Isoquinoline-1,3-Diones[J].Journal of Medicinal Chemistry,1997,40(4):449-454.
[5] ZHANG Min,XIE Ping,ZHAO Wannian,et al.Cascade Couplings of N-Alkyl-N-Methacryloyl Benza-Mides with Ethers and Benzenesulfonohydrazides to Generate Isoquinoline-1,3(2H,4H)-Dione Derivatives[J].The Journal of Organic Chemistry,2015,80(8):4 176-4 183.
[6] FU Wei,ZHU Mei,ZOU Guang,et al.Visible-Light-Mediated Radical Aryldifluoroacetylation of N-Arylacrylamides to Give Difluoroacetylated Oxindoles[J].Asian Journal of Organic Chemistry,2014,3(12):1 273-1 276.
[7] WANG Yaofeng,QIU Jiashen,KONG Dejie,et al.Silver-Mediated Radical Trifluoromethylarylation of Activated Alk-Enes for the Synthesis of Oxindoles Bearing a CF3 Group[J].Synlett,2014,25(12):1 731-1 734.
[8] XU Pan,HU Kaidong,GU Zhangxi,et al.Visible Light Promoted Carbodifluoroalkylation of Allylic Alcohols via Concomitant 1,2-Aryl Migration[J].Chemical Communication,2015,51:7 222-7 225.
[9] LI Lei,DENG Min,TAN Bin,et al.Metal-Free Direct Intramolecular Carbotrifluoromethylation of Alkenes to Functionalized Trifluoromethyl Azaheterocycles[J].Organic Letters,2014,16(2):504-507.
[10] WANG Qingkong,MARIA CASIMIRO,NOELIA FUENTES,et al.Metal-Free Aryltrifluoromethylation of Activated Alkenes[J].Angewandte Chemie International Edition,2013,52(49):13 086-13 090.
[11] ZHANG Lewei,YANG Chao,XU Zhongzhao,et al.Difunctionalization of Alkenes via the Visible-Light-Induced Trifluoromethylarylation/1,4-Aryl Shift/Desulfonylation Cascade Reactions[J].The Journal of Organic Chemistry,2015,80(11):5 730-5 736.
[12] NAGIB DAVID A,SCOTT MARK E,MACMILLAN DAVID W C.Enantioselective α-Trifluoromethylation of Alde Hydes via Photoredox Organocatalysis[J].Journal of the American Chemical Society,2009,131(31):10 875-10 877.
[13] NGUYEN JOHN D,TUCKER JOSEPH W,KONIECZYNSKA MARIENA D,et al.Intermolecular Atom Transfer Radical Addition to Olefins Mediated by Oxidative Quenching of Photoredox Catalysts[J].Journal of the American Chemical Society,2011,133(6):4 160-4 163.
[14] YOSHIOKA EITO,KOHTANI SHIGERU,TANAKA ERI,et al.Carbon Radical Addition-Cyclization Reaction Induced by Ruthenium-Photocatalyst Under Visible Light Irradiation[J].Tetrahedron,2015,71(5):773-781.
[15] TANG Xiaojun,THOMOSON CHARLES S,DOLBIER WILLIAM R,et al.Photoredox-Catalyzed Tandem Radical Cyclization of N-Arylacrylamides:General Methods to Construct Fluorinated 3,3-Disubstituted 2-Oxindoles Using Fluoroalkylsulfonyl Chlorides[J].Organic Letters,2014,16(17):4 594-4 597.
[16] SAHOO BASUEDV,HOPKINSON MATTHEW N,GLORIUS FRANK,et al.Combining Gold and Photoredox Catalysis:Visible Light Mediated Oxy-and Aminoarylation of Alkenes[J].Journal of the American Chemical Society,2013,135(15):5 505-5 508.
[17] TANG Shi,LI Zhihao,WANG Mingwei,et al.Metal-Free Cascade Cyclization of Alkenes Toward Perfluorinated Oxindoles[J].Organic Biomolecular Chemistry,2015,13(3):5 285-5 288.