Synthesis of Perinaphthenones via BF3.Et2O Mediated One-Pot Cascade 4,5-Annulation Reactions of 1-Naphthols and Ynones

被引:5
|
作者
Kuo, Chun-Wei [1 ]
Rao, Naidu Sambasiva [1 ]
Patil, Prakash Bhimrao [1 ]
Chiang, Ting-Ta [1 ]
Kavala, Veerababurao [1 ]
Yao, Ching-Fa [1 ]
机构
[1] Natl Taiwan Normal Univ, Dept Chem, 88,Sec 4,Ting Zhou Rd, Taipei 116, Taiwan
关键词
Perinaphthenones; Periannulation; alpha-naphthol; Ynones; Solvent-Free; NAPHTHOLS; DEAROMATIZATION; PHENOLS; ACID; 4-PHENYLPHENALENONES; PHENYLPHENALENONE; PHENALENONES; PHYTOALEXIN; DERIVATIVES; ANNULATION;
D O I
10.1002/adsc.202001558
中图分类号
O69 [应用化学];
学科分类号
081704 ;
摘要
C-4-C-5 periannulation of 1-naphthols and ynones via (BF3Et2O)-Et-. mediated one-pot cascade under metal and solvent-free conditions have been developed for the synthesis of perinaphthenones. Furthermore, this strategy features the formation of new periannulation at C-4-C-5 positions of alpha-naphthol, synthesis of highly substituted perinaphthenones, broad substrate scope, readily available starting materials and good to moderate yields. The perinaphthenones products synthesized here have exhibited interesting photo physical properties
引用
收藏
页码:1935 / 1943
页数:9
相关论文
共 50 条
  • [31] ONE-POT SYNTHESIS OF ISOINDOLIN-1-ONES FROM NITROARENES AND o-PHTHALALDEHYDE VIA INDIUM-MEDIATED REDUCTIVE CONDENSATION REACTIONS
    Kim, Eungyung
    Jeong, Mingyeong
    Lee, Byung Min
    Kim, Byeong Hyo
    HETEROCYCLES, 2018, 96 (10) : 1759 - 1770
  • [32] Synthesis of the complex bridged 1,5-oxazabicycles via one-pot reactions of 4,5-diazafluoren-9-one, alkyl halides, and cyclic 1,3-diketone
    L. Hui
    S. Gao
    C. G. Yan
    Chemistry of Heterocyclic Compounds, 2012, 48 : 658 - 665
  • [33] Tandem Knoevenagel-[3+2] cycloaddition-elimination reactions: one-pot synthesis of 4,5-disubstituted 1,2,3-(NH)-triazoles
    Ponpandian, Thanasekaran
    Muthusubramanian, Shanmugam
    TETRAHEDRON LETTERS, 2012, 53 (01) : 59 - 63
  • [34] Synthesis of the complex bridged 1,5-oxazabicycles via one-pot reactions of 4,5-diazafluoren-9-one, alkyl halides, and cyclic 1,3-diketone
    Hui, L.
    Gao, S.
    Yan, C. G.
    CHEMISTRY OF HETEROCYCLIC COMPOUNDS, 2012, 48 (04) : 658 - 665
  • [35] A one-pot diastereoselective synthesis of 1,3-diols and 1,3,5-triols via cascade reactions of arylalkynyl Grignard reagents with enol esters
    Jiao, Yinchun
    Zhao, Wenjing
    Deng, Shuang
    Tang, Zilong
    Liu, Wanqiang
    Wan, Yichao
    Zhong, Fuqi
    JOURNAL OF CHEMICAL RESEARCH, 2020, 44 (5-6) : 255 - 266
  • [36] Immobilization of La on THH-CO2H@Fe3O4 nanocomposite for the synthesis of one-pot multicomponent reactions
    Tamoradi, Taiebeh
    Kal-Koshvandi, AfsanehTaheri
    Karmakar, Bikash
    Maleki, Ali
    MATERIALS RESEARCH EXPRESS, 2021, 8 (05)
  • [37] One-pot synthesis of fused benzoxazino[1,2,3]triazolyl[4,5-c]quinolinone derivatives and their anticancer activity
    Narsimha, Sirassu
    Battula, Kumara Swamy
    Nukala, Satheesh Kumar
    Gondru, Ramesh
    Reddy, Yellu Narasimha
    Nagavelli, Vasudeva Reedy
    RSC ADVANCES, 2016, 6 (78) : 74332 - 74339
  • [38] Synthesis of Spiropyrrolines via One-Pot Tf2O-Mediated Amide Activation/Formal [3+2]-Cycloaddition of α-Formylamino Ketones
    Ho, Khanh-Toan
    Pierce, Joshua G.
    JOURNAL OF ORGANIC CHEMISTRY, 2024, 89 (18): : 13031 - 13037
  • [39] Direct Synthesis for Benzofuro[3,2-d]pyrimidin-2-Amines via One-Pot Cascade [4+2] Annulation/Aromatization between Benzofuran-Derived Azadienes and Carbodiimide Anions
    Wang, Chuan-Chuan
    Wang, Qing-Long
    Li, Yi-Hui
    Ren, Meng-Ru
    Hou, Xue-Hui
    Ma, Zhi-Wei
    Liu, Xue-Hua
    Chen, Ya-Jing
    CHEMISTRY-A EUROPEAN JOURNAL, 2024, 30 (68)
  • [40] One-Pot Cascade Reactions Leading to Pyrido[2′,1′:2,3]imidazo[4,5-c][1,2,3]triazolo[1,5-a]quinolines under Bimetallic Relay Catalysis with Air as the Oxidant
    Wang, Ze
    Li, Bin
    Zhang, Xinying
    Fan, Xuesen
    JOURNAL OF ORGANIC CHEMISTRY, 2016, 81 (15): : 6357 - 6363