Synthesis of Tetracyclic Benzoxazolo-indol-3-ones from Isatogens and Arynes through a [3+2]-Cycloaddition and Skeletal Reorganization

被引：0
|
作者：
Halnor, Swapnil V. [1 ,2 ]
Singh, Maneesha [1 ,2 ]
Dhote, Pawan S. [1 ,2 ]
Ramana, Chepuri V. [1 ,2 ]
机构：
[1] CSIR Natl Chem Lab, Div Organ Chem, Pune 411008, India
[2] Acad Sci & Innovat Res AcSIR, Ghaziabad 201002, India
来源：
JOURNAL OF ORGANIC CHEMISTRY | 2024年 / 89卷 / 20期
关键词：
IN-SITU GENERATION; ONE-POT SYNTHESIS; CYCLOADDITION REACTIONS; 1,3-DIPOLAR CYCLOADDITION; SELECTIVE SYNTHESIS; MODULAR SYNTHESIS; FACILE SYNTHESIS; N-ARYLATION; DERIVATIVES; EFFICIENT;
D O I：
10.1021/acs.joc.4c01667
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
The construction of an unprecedented tetracyclic benzoxazolo-indol-3-one scaffold has been executed through the [3 + 2]-cycloaddition of isatogens with arynes. The initially formed benzisoxazolo-indol-3-one intermediate undergoes a skeletal reorganization through a 1,3-sigmatropic shift/retro-Mannich reaction with the net formation of one C-N and two C-O bonds. The Lewis acid-catalyzed allylation of some of the resulting benzoxazolo-indol-3-ones resulted in oxazepino-indolones with promising photophysical properties.
引用
收藏
页码：14919 / 14928
页数：10
相关论文
共 50 条
  • [21] Asymmetric Synthesis of Tetrahydroquinolines through a [3+2] Cycloaddition Controlled by Dienamine Catalysis
    Li, Wenjun
    Wei, Jia
    Jia, Qianfa
    Du, Zhiyun
    Zhang, Kun
    Wang, Jian
    CHEMISTRY-A EUROPEAN JOURNAL, 2014, 20 (22) : 6592 - 6596
  • [22] Synthesis of Spiro[indazole-3,3′-indolin]-2′-ones via [3+2] Dipolar Cycloaddition of Arynes with 3-Diazoindolin-2-ones and Indazolo[2,3-c]quinazolin-6(5H)-ones by Subsequent Thermal Isomerization
    Cheng, Bin
    Zu, Bing
    Bao, Bian
    Li, Yun
    Wang, Renqi
    Zhai, Hongbin
    JOURNAL OF ORGANIC CHEMISTRY, 2017, 82 (15): : 8228 - 8233
  • [23] Sunlight-mediated [3+2] cycloaddition of azobenzenes with arynes: an approach toward the carbazole skeleton
    Zhang, Wenjie
    Bu, Jiahui
    Wang, Lei
    Li, Pinhua
    Li, Hongji
    ORGANIC CHEMISTRY FRONTIERS, 2021, 8 (18) : 5045 - 5051
  • [24] SYNTHESIS OF (+/-)-SEPTICINE AND (+/-)-TYLOPHORINE BY REGIOSELECTIVE [3+2] CYCLOADDITION
    IIDA, H
    TANAKA, M
    KIBAYASHI, C
    JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1983, (06) : 271 - 272
  • [25] A radical [3+2]-cycloaddition reaction for the synthesis of difluorocyclopentanones
    Tang, Nana
    Xu, Yan
    Niu, Tao
    Yang, Shan
    Dong, Hongchun
    Wu, Xinxin
    Zhu, Chen
    ORGANIC CHEMISTRY FRONTIERS, 2021, 8 (12): : 3118 - 3122
  • [26] General and efficient synthesis of 1,2-dihydropyrrolo[3,4-b]indol-3-ones via a formal [3+2] cycloaddition initiated by C-H activation
    Xing, Siyang
    Guo, Junsuo
    Wang, Yuhan
    Wang, Chenyu
    Wang, Kui
    Zhu, Bolin
    ORGANIC CHEMISTRY FRONTIERS, 2020, 7 (24) : 4057 - 4063
  • [27] TOTAL SYNTHESIS OF (+/-)-ABRESOLINE VIA [3+2]CYCLOADDITION
    TAKANO, S
    SHISHIDO, K
    HETEROCYCLES, 1982, 19 (08) : 1439 - 1441
  • [28] Synthesis of indol-3-yl-benzofurans and carbazoles via Cu(OTf)2-catalyzed [3+2] and [4+2] cycloaddition
    Chauhan, Amar Nath Singh
    Vini, Vikrant
    Kumar, Akhilesh
    Erande, Rohan D.
    ORGANIC & BIOMOLECULAR CHEMISTRY, 2024, 22 (33) : 6690 - 6694
  • [29] Chiral Phosphoric Acid Catalyzed [3+2] Cycloaddition and Tandem Oxidative [3+2] Cycloaddition: Asymmetric Synthesis of Substituted 3-Aminodihydrobenzofurans
    Gelis, Coralie
    Bekkaye, Mathieu
    Lebee, Clement
    Blanchard, Florent
    Masson, Geraldine
    ORGANIC LETTERS, 2016, 18 (14) : 3422 - 3425
  • [30] Synthesis of Functionalized Pyrrolizidines/Pyrrolidines Incorporating a Spirooxindole Motif through [3+2] Cycloaddition
    Sarrafi, Yaghoub
    Sadatshahabi, Olmidinesarzieh
    Hamzehloueian, Mahshid
    Alimohammadi, Kamal
    Tajbakhsh, Mahgol
    SYNTHESIS-STUTTGART, 2013, 45 (16): : 2294 - 2304
12345