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
  • [1] BF3-Et2O-Mediated One-Pot Synthesis of Acetylchromans from Polyhydroxyacetophenones and Isoprene/Allyl Alcohol
    Narender, T.
    Reddy, K. Papi
    Shweta
    SYNTHETIC COMMUNICATIONS, 2009, 39 (03) : 384 - 394
  • [2] Practical Pd(TFA)2-Catalyzed Aerobic [4+1] Annulation for the Synthesis of Pyrroles via "One-Pot" Cascade Reactions
    Yu, Yang
    Mang, Zhiguo
    Yang, Wei
    Li, Hao
    Wang, Wei
    CATALYSTS, 2016, 6 (11):
  • [3] One-pot synthesis of borolanes by reaction of aluminacyclopentanes with BF3•Et2O
    Khafizova, L. O.
    Khusainova, L. I.
    Tyumkina, T. V.
    Dzhemilev, U. M.
    RUSSIAN JOURNAL OF ORGANIC CHEMISTRY, 2012, 48 (06) : 755 - 760
  • [4] Synthesis of pyrido[2′,1′:2,3]imidazo[4,5-c]isoquinolines via a one-pot, three-component reaction
    Maleki, Ali
    Rezayan, Ali Hossein
    TETRAHEDRON LETTERS, 2014, 55 (10) : 1848 - 1850
  • [5] One-Pot Access to 3-Sulfonyl Flavones via K2CO3-Mediated Annulation of α-Sulfonyl o-Hydroxyacetophenones with Substituted Nitriles
    Chang, Meng-Yang
    Lin, Chun-Yi
    ADVANCED SYNTHESIS & CATALYSIS, 2023, 365 (24) : 4726 - 4733
  • [6] Tunable Synthesis of 3-Acyl-2-naphthols and 3-Substituted Isocoumarins via Jones Reagent Promoted Cascade Reactions of 2-(4-Hydroxy-but-1-ynyl)benzaldehydes
    He, Yan
    Zhang, Xinying
    Shen, Nana
    Fan, Xuesen
    JOURNAL OF ORGANIC CHEMISTRY, 2013, 78 (20) : 10178 - 10191
  • [7] One-pot Biginelli synthesis of 3,4-dihydropyrimidin-2(1H)-ones using nano-cellulose/BF3/Fe3O4
    Tabaei, Maryam Alsadat Mazloum
    Bamoniri, Abdolhamid
    Mirjalili, Bi Bi Fatemeh
    JOURNAL OF THE IRANIAN CHEMICAL SOCIETY, 2022, 19 (07) : 2679 - 2691
  • [8] Facile One-Pot Synthesis of 1-Amidoalkyl-2-Naphthols by RuCl2(PPh3)3-Catalyzed Multi-Component Reactions
    Zhu, Xiaoyan
    Lee, Yong Rok
    Kim, Sung Hong
    BULLETIN OF THE KOREAN CHEMICAL SOCIETY, 2012, 33 (08) : 2799 - 2802
  • [9] Direct Synthesis of Sulfinylated Benzofulvenes via BF3•Et2O-Promoted Cascade Reactions of Arylsulfinic Acids with 1,3-Enynes
    Zhang, Zhen
    Li, Anni
    Zhao, Beibei
    Li, Pinhua
    Wang, Lei
    Miao, Tao
    ORGANIC LETTERS, 2021, 23 (21) : 8204 - 8208
  • [10] One-pot synthesis of five substituted tetrahydropyridines using nano-Al2O3/BF3/Fe3O4 as a highly efficient nano-catalyst
    Babaei, Elaheh
    Mirjalili, Bi Bi Fatemeh
    RESEARCH ON CHEMICAL INTERMEDIATES, 2018, 44 (05) : 3493 - 3505