Diels-Alder反应合成氧化吲哚螺环化合物研究进展
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摘要
氧化吲哚螺环化合物是多种天然产物的核心骨架,具有抗疟、抗癌、避孕、抗高血压等多种生物活性和药物活性,因此受到有机化学家们的广泛关注。目前报道的氧化吲哚螺环化合物的合成方法主要有1,3-偶极环加成反应、多组分串联反应以及Diels-Alder反应等,其中Diels-Alder反应凭借其条件温和、选择性好等诸多优点,成为构建螺环化合物的高效方法。在手性催化和非手性催化两方面阐述了通过Diels-Alder反应合成氧化吲哚螺环化合物的研究方法,根据催化剂的不同对其进行了分类和总结,最后对氧化吲哚螺环化合物合成的发展趋势作出了展望。
Spirooxindoles are the core skeleton of many natural products.They have many biological and pharmaceutical activities,such as anti-malaria,anti-cancer,contraception,anti-hypertension and so on.Therefore,they have attracted extensive attention of organic chemists.At present,the main methods reported for synthesis the spirooxindoles are 1,3-dipolar cycloaddition reaction,multi-component series reaction and Diels-Alder reaction.As an efficient method for the synthesis of spirooxindoles,Diels-Alder reaction has great advantages such as mild reaction conditions and high selectivity.Recent Diels-Alder reaction in the synthesis of spirooxindole was described by the type of catalyst.In addition,the development trend of spirooxindoles was prospected.
Spirooxindoles are the core skeleton of many natural products.They have many biological and pharmaceutical activities,such as anti-malaria,anti-cancer,contraception,anti-hypertension and so on.Therefore,they have attracted extensive attention of organic chemists.At present,the main methods reported for synthesis the spirooxindoles are 1,3-dipolar cycloaddition reaction,multi-component series reaction and Diels-Alder reaction.As an efficient method for the synthesis of spirooxindoles,Diels-Alder reaction has great advantages such as mild reaction conditions and high selectivity.Recent Diels-Alder reaction in the synthesis of spirooxindole was described by the type of catalyst.In addition,the development trend of spirooxindoles was prospected.
引文
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[2]DING K,LU Y P,WANG S M,et al.Structure-based design of potent non-peptide MDM2 inhibitors[J].J.Am.Chem.Soc.,2005,127(29):10 130-10 131.
[3]LIN H,DANISHEFSKY S J.Gelsemine:a thought-provoking target for total sythesis[J].Angew.Chem.Int.Ed.,2003,42(11):36-51.
[4]VENKATESAN H,DAVIS M C,ALTAS Y,et al.Total synthesis of SR 121463 A,a highly potent and selective vasopressin V2 receptor antagonist[J].J.Org.Chem.,2001,11(66):3 653-3 661.
[5]FENSOME A,ADAMS W R,ADAMS A L,et al.Design,synthesis,and SAR of new pyrrole-oxindole progesterone receptor modulators leading to 5-(7-Fluoro-3,3-dimethyl-2-oxo-2,3-dihydro-1H-indol-5-yl)-1-methyl-1H-pyrrole-2-carbonitrile(WAY-255348)[J].J.Med.Chem.,2008,51(6):1 861-1 873.
[6]ROTTMANN M,MCNAMARA C,YEUNG B K S,et al.Spiroindolones,a new and potent chemotype for the treatment of malaria[J].Science,2010,329(5 996):1 175-1 180.
[7]DING K,LU Y P,WANG S M,et al.Structure-based design of spiro-oxindoles as potent,specific small-molecule inhibitors of the MDM2-p53 interaction[J].J.Med.Chem.,2006,49(12):3 432-3 435.
[8]NARAYAN R,POTOWSKI M,JIA Z,et al.Catalytic enantioselective 1,3-dipolar cycloadditions of azomethine ylides for biology-oriented synthesis[J].Acc.Chem.Res.,2014,47(4):1 296-1 310.
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[10]YAN L J,WANG Y C.Recent advances in green synthesis of 3,3′-spirooxindoles via isatin based one-pot multicomponent cascade reactions in aqueous medium[J].Chemistryselect,2016,1(21):6 948-6 960.
[11]ZIARANI G M,NASABA N H,LASHGARI N.Synthesis of heterocyclic scaffolds through 6-aminouracil-involved multicomponent reactions[J].RSC Adv.,2016,6(25):38 827-38 848.
[12]BALLANTINE J A,JOHNSON A W,KATNER A S.The reaction of isatin with acetic anhydride and pyridine[J].J.Chem.Soc,1964,2:3 323-3 330.
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[14]KUNISUKE O,HIROTERU S,MORIHIDE K,et al.Diels-Alder reaction of 3-methoxycarbonylmethylene-2-oxoindoline derivatives with unsymmetrical butadienes[J].Chem.Lett.,1979,3(8):213-216.
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[29]QUE Y L,LI T J,YU C X,et al.Enantioselective assembly of spirocyclic oxindole dihydropyranones through NHC-catalyzed cascade reaction of isatins with N-hydroxybenzotriazole esters of α,β-unsaturated carboxylic acid[J].J.Org.Chem.,2015,80(6):3 289-3 294.
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[31]HUANG L J,WENG J,WANG S,et al.Organocatalytic Diels-Alder reaction of 2-vinylindoles with methyleneindolinones:an efficient approach to functionalized carbazolespirooxindoles[J].Adv.Synth.Catal.,2015,357(5):993-1 003.
[32]RAMACHARY D B,REDDY P S,SHRUTHI K S,et al.A Br?nsted acid-primary amine as a synergistic catalyst for stereoselective asymmetric Diels-Alder reactions[J].Eur.J.Org.Chem.,2016,31(7):5 220-5 226.
[33]LI G L,LIANG T,WOJTAS L,et al.An asymmetric Diels-Alder reaction catalyzed by chiral phosphate magnesium complexes:highly enantioselective synthesis of chiral spirooxindoles[J].Angew.Chem.Int.Ed.,2013,52(17):4 628-4 632.
[34]ZHENG J F,LIN L L,FU K,et al.Asymmetric hetero-Diels-Alder reaction of danishefskys diene with α-ketoesters and isatins catalyzed by a chiral N,N′-dioxide/Magnesium(Ⅱ) complex[J].Chem.Eur.J.,2014,20(44):14 493-14 498.