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
  • [21] Transition-Metal-Free C2-H Sulfonylation of Quinoline N-Oxides via Insertion of Sulfur Dioxide
    Cai, Heng
    Yang, Huiyong
    Xu, Jun
    Bao, Hanyang
    Huang, Lin
    Zhang, Hongdou
    Zhang, Pengfei
    Li, Wanmei
    ASIAN JOURNAL OF ORGANIC CHEMISTRY, 2019, 8 (11) : 2105 - 2108
  • [22] Metal-free intramolecular transannulation of N,3-diaryloxirane-2-carboxamides: a concise and versatile route to 3-arylquinolin-2(1H)-ones
    Mamedov, Vakhid A.
    Mamedova, Vera L.
    Kadyrova, Saniya F.
    Khikmatova, Gul'naz Z.
    Gubaidullin, Aidar T.
    Rizvanov, Il'dar Kh.
    Latypov, Shamil K.
    TETRAHEDRON, 2015, 71 (18) : 2670 - 2679
  • [23] Monocyclic 1,2,3-triazin-4(3H)-ones:: Synthesis, structure and photochemical behaviour
    Celli, Angela Maria
    Ferrini, Serena
    Ponticelli, Fabio
    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2006, 2006 (13) : 3021 - 3025
  • [24] One-pot synthesis of 5-arylamino-1,3,4-selenadiazol-2(3H)-ones from arylisoselenocyanates
    Xie, Yuanyuan
    Yang, Ping
    Chen, Xiaodong
    JOURNAL OF CHEMICAL RESEARCH, 2012, (07) : 421 - 424
  • [25] Transition-Metal-Free Continuous-Flow Synthesis of 2,5-Diaryl Furans: Access to Medicinal Building Blocks and Optoelectronic Materials
    Grantham, Helena F.
    Lee, Robert J.
    Wardas, Grzegorz M.
    Mistry, Jai-Ram
    Elsegood, Mark R. J.
    Wright, Iain A.
    Pritchard, Gareth J.
    Kimber, Marc C.
    JOURNAL OF ORGANIC CHEMISTRY, 2023, 89 (01) : 484 - 497
  • [26] Regioselective Transition-Metal-Free C(sp2)-H Borylation: A Subject of Practical and Ongoing Interest in Synthetic Organic Chemistry
    Rej, Supriya
    Chatani, Naoto
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2022, 61 (44)
  • [27] Transition-metal-free C-H amidation and chlorination: synthesis of N/N'-mono-substituted imidazopyridin-2-ones from N-pyridyl-Nhydroxylamine intermediates
    Lee, Katarzyna N.
    Spiegowski, Dominique N.
    Lee, Johnny W.
    Lim, Sanghyun
    Zhao, Fuhua
    Ngai, Ming-Yu
    CHEMICAL COMMUNICATIONS, 2018, 54 (50) : 6935 - 6938
  • [28] Microwave-assisted Oxidation of 3,4-Dihydropyrimidin-2(1H)-ones
    Memarian, Hamid Reza
    Sabzyan, Hassan
    Farhadi, Asadollah
    ZEITSCHRIFT FUR NATURFORSCHUNG SECTION B-A JOURNAL OF CHEMICAL SCIENCES, 2009, 64 (05): : 532 - 540
  • [29] Synthesis of 2-(1,2,4-oxadiazol-3-yl)quinazolin-4(3H)-ones from diaminoglyoxime-based nitrones
    Rahim Hosseinzadeh-Khanmiri
    Abolghasem Moghimi
    Ahmad Shaabani
    Hassan Valizadeh
    Seik Weng Ng
    Molecular Diversity, 2015, 19 : 501 - 510
  • [30] Synthesis of 2-(1,2,4-oxadiazol-3-yl)quinazolin-4(3H)-ones from diaminoglyoxime-based nitrones
    Hosseinzadeh-Khanmiri, Rahim
    Moghimi, Abolghasem
    Shaabani, Ahmad
    Valizadeh, Hassan
    Ng, Seik Weng
    MOLECULAR DIVERSITY, 2015, 19 (03) : 501 - 510
12345