Transition-metal-free decarbonylation-oxidation of 3-arylbenzofuran-2(3H)-ones: access to 2-hydroxybenzophenones

被引:0
|
作者
Dhotare, Bhaskar B. [1 ]
V. Kanojia, Seema [1 ]
Sakhiya, Chahna K. [2 ]
Wadawale, Amey [3 ]
Goswami, Dibakar [1 ,4 ]
机构
[1] Bhabha Atom Res Ctr, Bioorgan Div, Trombay 400085, Mumbai, India
[2] NMIMS Sunandan Divatia Sch Sci, Vile Parle, Mumbai 400056, India
[3] Bhabha Atom Res Ctr, Chem Div, Mumbai 400085, India
[4] Homi Bhabha Natl Inst, Anushaktinagar, Mumbai 400094, India
来源
BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY | 2024年 / 20卷
关键词
decarbonylation-oxidation; hydroperoxide; 2-hydroxybenzophenone; transition-metal-free; UV-protection; REARRANGEMENT; MECHANISM;
D O I
10.3762/bjoc.20.223
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A transition-metal-free decarbonylation-oxidation protocol for the conversion of 3-arylbenzofuran-2(3H)-ones H )-ones to 2-hydroxybenzophenones under mild conditions has been developed. NMR studies confirmed the role of in-situ-generated hydroperoxide in the conversion. The protocol was applied to a diverse range of substrates to access the target products in good to excellent yields. A structure-activity study for the 5-substituted-2-hydroxybenzophenones towards UV-protection abilities has been verified by mathematical calculations.
引用
收藏
页码:2655 / 2667
页数:13
相关论文
共 50 条
  • [41] Domino reactions in water for the stereoselective synthesis of novel spiro dihydro-2′H[indene-2,3′-thiophen]-1(3H)-ones with three contiguous stereocenters
    Kumar, Sundaravel Vivek
    Prasanna, Pitchaimani
    Perumal, Subbu
    TETRAHEDRON LETTERS, 2013, 54 (48) : 6651 - 6655
  • [42] Transition-Metal-Free Direct Arylation and Esterification Reaction of Unprotected Indolylcarboxylic Acid Derivatives: A New Entry to 2-(1H-Indol-2-yl)-5-(phenylthio)-1,3,4-oxadiazoles and Aryl 1H-Indole-2-carboxylates
    Wang, Dawei
    Ge, Chenyang
    Yu, Xin
    Wan, Huida
    Xu, Xiang
    SYNLETT, 2016, 27 (18) : 2616 - 2620
  • [43] Transition-Metal Free C(sp3)-H Sulfonylation for the Synthesis of 2-Sulfolmethyl Quinolines from 2-Methylquinolines and Sulfonyl Hydrazides
    Li, Qian
    Zhu, Haibo
    Yang, Liu
    Meng, Jia
    Xie, Zongbo
    Le, Zhang-Gao
    ASIAN JOURNAL OF ORGANIC CHEMISTRY, 2022, 11 (12)
  • [44] Transition metal-free synthesis of quinolino[2′,3′:3,4]pyrazolo[5,1-b]quinazolin-8(6H)-ones via cascade dehydrogenation and intramolecular N-arylation
    Morteza Shiri
    Majid M. Heravi
    Hoda Hamidi
    Mohammad A. Zolfigol
    Zahra Tanbakouchian
    Atefeh Nejatinezhad-Arani
    Suhas A. Shintre
    Neil A. Koorbanally
    Journal of the Iranian Chemical Society, 2016, 13 : 2239 - 2246
  • [45] Design, Synthesis, Pharmacological Evaluation of Quinazolin-4(3H)-Ones Bearing Urea Functionality as Potential VEGFR-2 Inhibitors
    Al-Sanea, Mohammad M.
    Hafez, Hani M.
    AB Mohamed, Ahmed
    El-Shafey, Hamed W.
    Elgazar, Abdullah A.
    Tawfik, Samar S.
    Ewes, Wafaa A.
    Hussein, Shaimaa
    Alsahli, Tariq G.
    Hamdi, Abdelrahman
    DRUG DESIGN DEVELOPMENT AND THERAPY, 2024, 18 : 5109 - 5127
  • [46] Transition metal-free synthesis of quinolino[2',3':3,4]pyrazolo[5,1-b]quinazolin-8(6H)-ones via cascade dehydrogenation and intramolecular N-arylation
    Shiri, Morteza
    Heravi, Majid M.
    Hamidi, Hoda
    Zolfigol, Mohammad A.
    Tanbakouchian, Zahra
    Nejatinezhad-Arani, Atefeh
    Shintre, Suhas A.
    Koorbanally, Neil A.
    JOURNAL OF THE IRANIAN CHEMICAL SOCIETY, 2016, 13 (12) : 2239 - 2246
  • [47] Polycyclic N-Heterocyclic Compounds. Part 60: Reactions of 3-(2-Cyanophenyl)quinazolin-4(3H)-ones with Primary Amines
    Okuda, Kensuke
    Tagata, Tsuyoshi
    Kashino, Setsuo
    Hirota, Takashi
    Sasaki, Kenji
    CHEMICAL & PHARMACEUTICAL BULLETIN, 2009, 57 (11) : 1296 - 1299
  • [48] Chiral phosphine-catalyzed asymmetric allylic alkylation of 3-substituted benzofuran-2(3H)-ones or oxindoles with Morita-Baylis-Hillman carbonates
    Wang, De
    Yang, Yuan-Liang
    Jiang, Jia-Jun
    Shi, Min
    ORGANIC & BIOMOLECULAR CHEMISTRY, 2012, 10 (35) : 7158 - 7166
  • [49] Application of N-Acylbenzotriazoles in the Synthesis of 5-Substituted 2-Ethoxy-1,3,4-oxadiazoles as Building Blocks toward 3,5-Disubstituted 1,3,4-Oxadiazol-2(3H)-ones
    Wet-osot, Sirawit
    Phakhodee, Wong
    Pattarawarapan, Mookda
    JOURNAL OF ORGANIC CHEMISTRY, 2017, 82 (18) : 9923 - 9929
  • [50] Piperidine-Mediated [3+3] Cyclization of 2-Amino-4H- nchromen-4-ones and 2-Benzylidenemalononitriles: To Access 2-Aminochromeno[2,3-b]pyridine Derivatives
    Zhang, Dan
    Luo, Naili
    Gan, Jianbo
    Wan, Xinyi
    Wang, Cunde
    JOURNAL OF ORGANIC CHEMISTRY, 2021, 86 (13) : 9218 - 9224