Copper-Catalyzed Annulation of O-Acyl Oximes with Cyclic 1,3-Diones for the Synthesis of 7,8-Dihydroindolizin-5(6H)-ones and Cyclohexanone-Fused Furans

被引：10
|
作者：
Yang, Hai-Tao [1 ]
Zhou, Su-Qing [1 ]
Chen, Dan-Mei [1 ]
Hu, Zi-Jun [1 ]
Qiang, Xiao-Qi [1 ]
Song, Xiao-Qing [1 ]
Tan, Sheng [1 ]
Jiang, Wei-Hua [1 ]
Sun, Yong-Qiang [2 ]
Miao, Chun-Bao [1 ]
机构：
[1] Changzhou Univ, Sch Petrochem Engn, Jiangsu Key Lab ofAdvanced Catalyt Mat & Technol, Jiangsu Prov Key Lab Fine Petrochem Engn, Changzhou 213164, Jiangsu, Peoples R China
[2] Changzhou Siyao Pharmaceut Co Ltd, Changzhou 213018, Jiangsu, Peoples R China
来源：
ORGANIC LETTERS | 2023年
关键词：
3-COMPONENT CASCADE ANNULATION; ACETATES; 1-ACYL-1H-PYRROLES; CYCLIZATIONS; HETEROCYCLES; ALKALOIDS; INDOLES;
D O I：
10.1021/acs.orglett.3c00003
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
A copper-catalyzed annulation of O-acyl oximes with cyclic 1,3-diones has been developed for the concise synthesis of 7,8-dihydroindolizin-5(6H)-ones and cyclohexanone-fused furans through the substituent-controlled selective radical coupling process. 2-Alkyl cyclic 1,3-diones undergo C-C radical coupling, while 2-unsubstituted cyclic 1,3-diones undergo C-O radical coupling.
引用
收藏
页码：838 / 842
页数：5
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共 13 条
  • [1] Copper-Catalyzed Cascade Annulation of Malonate-Tethered O-Acyl Oximes with Cyclic 1,3-Dicarbonyl Compounds for the Synthesis of Spiro-Pentacyclic Derivatives
    Wang, Kun
    Guan, Hong-Rong
    Ren, Wen-Long
    Yang, Hai-Tao
    Miao, Chun-Bao
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 2021, 86 (17): : 12309 - 12317
  • [2] REACTION OF "2-DIMETHYLAMINOMETHYLENE-1,3-DIONES WITH DINUCLEOPHILES .3. SYNTHESIS OF 5-ACYLPYRIMIDINES AND 7,8-DIHYDROQUINAZOLIN-5(6H)-ONES
    MOSTI, L
    MENOZZI, G
    SCHENONE, P
    [J]. JOURNAL OF HETEROCYCLIC CHEMISTRY, 1983, 20 (03) : 649 - 654
  • [3] Copper-Catalyzed [3+2] Annulation of O-Acyl Oximes with 4-Sulfonamidophenols for the Synthesis of 5-Sulfonamidoindoles and 2-Amido-5-sulfonamidobenzofuran-3(2H)-ones
    Hu, Zi-Jun
    Chen, Wei
    Lyu, Xinyu
    Zhang, Hui-Peng
    Chen, Si-Wei
    Ding, Xian-Heng
    Yu, Cang-Hai
    Cui, Zhen
    Miao, Chun-Bao
    Yang, Hai-Tao
    [J]. ORGANIC LETTERS, 2024, 26 (20) : 4229 - 4234
  • [4] THE CONVERSION OF CYCLOHEXANE-1,3-DIONES OR THEIR ENAMINONE DERIVATIVES INTO 7,8-DIHYDROQUINOLIN-5(6H)-ONES AND 3 BIS-VINYLOGOUS-IMIDE BY-PRODUCTS
    GREENHILL, JV
    MOTEN, MA
    HANKE, R
    BREITMAIER, E
    [J]. JOURNAL OF CHEMICAL RESEARCH-S, 1981, (03): : 66 - 67
  • [5] An efficient synthesis of 2-hydroxy-7,8-dihydroquinolin-5(6H)-ones and 7,8-dihydroquinoline-2,5(1H,6H)-diones from Morita-Baylis-Hillman adduct acetates
    Zhong, Weihui
    Lin, Fuliang
    Chen, Ren'er
    Su, Weike
    [J]. SYNTHESIS-STUTTGART, 2008, (16): : 2561 - 2568
  • [6] Synthesis of Stable N-H Imines with a Benzo[7,8]indolizine Core and Benzo[7,8]indolizino[1,2-c]quinolines via Copper-Catalyzed Annulation of α,β-Unsaturated O-Acyl Ketoximes with Isoquinolinium N-Ylides
    Miao, Chun-Bao
    Qiang, Xiao-Qi
    Xu, Xiaoli
    Song, Xiao-Qing
    Zhou, Su-Qing
    Lyu, Xinyu
    Yang, Hai-Tao
    [J]. ORGANIC LETTERS, 2022, 24 (21) : 3828 - 3833
  • [7] Synthesis of novel 3-(1,3-thiazol-2-yl)-7,8-dihydroquinoline-2,5(1H,6H)-diones
    S. G. Dzhavakhishvili
    N. Yu. Gorobets
    V. N. Chernenko
    V. I. Musatov
    S. M. Desenko
    [J]. Russian Chemical Bulletin, 2008, 57
  • [8] Synthesis of novel 3-(1,3-thiazol-2-yl)-7,8-dihydroquinoline-2,5(1H,6H)-diones
    Dzhavakhishvili, S. G.
    Gorobets, N. Yu.
    Chernenko, V. N.
    Musatov, V. I.
    Desenko, S. M.
    [J]. RUSSIAN CHEMICAL BULLETIN, 2008, 57 (02) : 422 - 427
  • [9] SYNTHESIS OF SUBSTITUTED 7,12-DIHYDROINDOLO[3,2-B][1,4]-BENZODIAZEPIN-5(6H)-ONES AND 1,2,3,4,5,6-HEXAHYDRO[1,3]-DIAZEPINO[5,6-B]INDOLE-1,5-DIONES
    HIREMATH, SP
    BADAMI, PS
    PUROHIT, MG
    [J]. INDIAN JOURNAL OF CHEMISTRY SECTION B-ORGANIC CHEMISTRY INCLUDING MEDICINAL CHEMISTRY, 1984, 23 (11): : 1058 - 1063
  • [10] Synthesis of fused dihydropyrimidinones from cyclic-1,3-dicarbonyl compounds:: Modified Biginelli synthesis of 1,2,3,4,5,6,7,8-octahydroquinazolinediones and 3,4-dihydro-1H-indeno[1,2-d]pyrimidine-2,5-diones
    Shanmugam, P
    Sabastein, C
    Perumal, PT
    [J]. INDIAN JOURNAL OF CHEMISTRY SECTION B-ORGANIC CHEMISTRY INCLUDING MEDICINAL CHEMISTRY, 2004, 43 (01): : 135 - 140
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