Synthesis of Oxindoles via SmI 2 -Promoted Reduction of 2-Nitrophenylacetic Acids

被引：3
作者：
Wang, Pengkai [1 ]
Zhang, Songlin [1 ]
机构：
[1] Soochow Univ, Coll Chem Chem Engn & Mat Sci, Key Lab Organ Synth Jiangsu Prov, Dushu Lake Campus, Suzhou 215123, Peoples R China
来源：
SYNTHESIS-STUTTGART | 2024年 / 56卷 / 01期
基金：
中国国家自然科学基金;
关键词：
samarium diiodide; single electron transfer reagent; oxindoles; SUBSTITUTED OXINDOLES; BIOLOGICAL EVALUATION; DERIVATIVES; INHIBITORS; DISCOVERY; EFFICIENT; ARYLATION; INDOLES; DESIGN; AMINES;
D O I：
10.1055/a-2175-1008
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
The reduction of 2-nitrophenylacetic acids to oxindoles promoted by SmI2 is reported for the first time. This reaction involving the reduction of nitro group proceeds through N-O bond cleavage and direct condensation with the neighboring carboxyl group. From a synthetic point of view, a new method for the synthesis of oxindoles in mild neutral conditions is developed.
引用
收藏
页码：171 / 178
页数：8
相关论文
共 50 条
  • [41] Synthesis of xanthenone fused spiro pyrrolidine oxindoles via multicomponent [3+2] cycloaddition reactions
    Paramasivam, Gurusivam
    Palanichamy, Baskaralingam
    Paramathevar, Nagaraaj
    MOLECULAR DIVERSITY, 2025,
  • [42] Deciphering Intermediates and Additives Effect on the Reduction of Nitrobenzene by SmI2
    Surasani, Seshi Reddy
    Maity, Sandeepan
    CHEMISTRYSELECT, 2017, 2 (02): : 598 - 603
  • [43] Electron transfer reduction of unactivated esters using SmI2-H2O
    Szostak, Michal
    Spain, Malcolm
    Procter, David J.
    CHEMICAL COMMUNICATIONS, 2011, 47 (37) : 10254 - 10256
  • [44] Selective Synthesis of α,α-Dideuterio Alcohols by the Reduction of Carboxylic Acids Using SmI2 and D2O as Deuterium Source under SET Conditions
    Szostak, Michal
    Spain, Malcolm
    Procter, David J.
    ORGANIC LETTERS, 2014, 16 (19) : 5052 - 5055
  • [45] Direct Synthesis of N-Monosubstituted Benzimidazol-2-ones via Ph 3 P-I 2 -Mediated Reaction of Hydroxamic Acids
    Wiriya, Nittaya
    Yamano, Dolnapa
    Hongsibsong, Surat
    Pattarawarapan, Mookda
    Phakhodee, Wong
    SYNLETT, 2022, 33 (14) : 1468 - 1472
  • [46] Catalytic asymmetric synthesis of spirocyclobutyl oxindoles and beyond via [2+2] cycloaddition and sequential transformations
    Zhong, Xia
    Tan, Jiuqi
    Qiao, Jianglin
    Zhou, Yuqiao
    Lv, Cidan
    Su, Zhishan
    Dong, Shunxi
    Feng, Xiaoming
    CHEMICAL SCIENCE, 2021, 12 (29) : 9991 - 9997
  • [47] Alternative synthetic path to (-)-adalinine via a SmI2-promoted fragmentation of a 3-oxopyrrolidine derivative
    Honda, Toshio
    Hisa, Chihiro
    TETRAHEDRON LETTERS, 2009, 50 (32) : 4654 - 4657
  • [48] Tf2O-Promoted Synthesis of Ureas, Carbamates and Thiocarbamate via Lossen Rearrangement: A Mechanistic Insight
    Chetankumar, Eti
    Srinivasulu, Chinthaginjala
    Periyasamy, Ganga
    Sureshbabu, Vommina V.
    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2024, 27 (15)
  • [49] Application of SmI2 in organic synthesis
    Zhao, JR
    Jia, XS
    Zhai, HB
    CHINESE JOURNAL OF ORGANIC CHEMISTRY, 2003, 23 (06) : 499 - 512
  • [50] Synthesis of Multifunctional 2-Aminobenzimidazoles on DNA via Iodine-Promoted Cyclization
    Su, Liqiang
    Feng, Jing
    Peng, Ting
    Wan, Jinqiao
    Fan, Jing
    Li, Jin
    O'Connell, Jonathan
    Lancia, David R., Jr.
    Franklin, G. Joseph
    Liu, Guansai
    ORGANIC LETTERS, 2020, 22 (04) : 1290 - 1294
12345