新型甘油拼接3-四取代氧化吲哚的无催化剂无溶剂合成
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摘要
以3-氯氧化吲哚为原料,在无催化剂、无溶剂条件下于80℃发生亲核取代反应,合成了10个新型的甘油拼接3-四取代氧化吲哚,收率54%～72%,dr值10/9～>10/7,其结构经~1H NMR,~(13)C NMR和HR-MS(ESI-TOF)表征。
Ten novel glycerol-fused 3-tetrasubstituted oxindoles were synthesized via nucleophilic substitution reaction from 3-chloroxindoles under solvent-and catalyst-free condition at 80 ℃ for 24 h. The yields and dr were 54%～72% and 10/91～10/7, respectively. The structures were characterized by ~1H NMR, ~(13)C NMR and HR-MS(ESI-TOF).
Ten novel glycerol-fused 3-tetrasubstituted oxindoles were synthesized via nucleophilic substitution reaction from 3-chloroxindoles under solvent-and catalyst-free condition at 80 ℃ for 24 h. The yields and dr were 54%～72% and 10/91～10/7, respectively. The structures were characterized by ~1H NMR, ~(13)C NMR and HR-MS(ESI-TOF).
引文
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[2] HUM P C,TAKASHI T,JU C E,et al.Glycerol-induced renal damage improved by 7-O-galloyl-D-sedoheptulose treatment through attenuating oxidative stress[J].Biological & Pharmaceutical Bulletin,2012,35:34-41.
[3] TORU I,EIKO F,JUNICHI K.Water-soluble constituents of anise:New glucosides of anethole glycol and its related compounds[J].Chemical & Pharmaceutical Bulletin,2002,50:1460-1466.
[4] THOMAS J S,WINFRIED B.A convenient synthesis of (2R)-glyceryl-β-D-galactopyranoside[J].Journal of Biological Chemistry,1973,248:6571-6574.
[5] RUBERTO G,TRINGALI C.Secondary metabolites from the leaves of feijoa sellowiana berg[J].Phytochemistry,2004,65:2947-2951.
[6] ISHIKAWA T,FUJIMATU E,KITAJIMA J.Water-soluble constituents of anise:New glucosides of anethole glycol and its related compounds[J].Chem Pharm Bull,2002,50:1460-1466.
[7] DOUNAY A B,OVERMAN L E.The asymmetric intramolecular Heck reaction in natural product total synthesis[J].Chem Rev,2003,103:2945-2964.
[8] LIN H,DANISHEFSKY S J.Gelsemine:A thought-provoking target for total synthesis[J].Angew Chem Int Ed,2003,42:36-51.
[9] GALLIFORD C V,Scheidt K A.Pyrrolidinyl-spirooxindole natural products as inspirations for the development of potential therapeutic agents[J].Angew Chem Int Ed,2007,46:8748-8758.
[10] YANG M C,PENG C,HUANG H,et al.Organocatalytic asymmetric synthesis of spiro-oxindole piperidine derivatives that reduce cancer cell proliferation by inhibiting MDM2-p53 interaction[J].Org Lett,2017,19:6752-6755.
[11] WANG S,CHEN S,GUO Z,et al.Synthesis of spiro-tetrahydrothiopyran-oxindoles by Michael-Aldol cascade reactions:discovery of potential P53-MDM2 inhibitors with good antitumor activity[J].Org Biomol Chem,2018,16:625-634.
[12] 刘雄伟,周根,姚震,等.异噁唑拼接吡咯螺环氧化吲哚化合物的合成及其抗肿瘤活性[J].合成化学,2016,24(5):389-392.
[13] 彭礼军,周根,韩朔楠,等.新型芳姜黄酮拼合吡咯螺环氧化吲哚类化合物的合成及其抗肿瘤活性[J].合成化学,2016,24(8):669-672.
[14] 杨楷模,刘欢欢,陈智勇,等.3-卤氧化吲哚参与胺基化反应合成3-胺基四取代氧化吲哚[J].合成化学,2018,26(4):276-279.
[15] 韦启迪,杨楷模,岳静,等.新型3-吗啉-3-四取代氧化吲哚的合成[J].合成化学,2018,26(6):429-432.
[16] 王关炼,杨楷模,陈爽楠,等.新型3-哌啶/吡咯烷氧化吲哚的合成[J].合成化学,2018,26(8):602-606.