The synthesis of dibenzazocines via tandem dinucleophilic addition of phenols to quinolinium salts

被引:17
|
作者
Moghaddam, Firouz Matloubi [1 ]
Saeidian, Hamdollah [1 ,2 ]
Kiamehr, Mostafa [1 ]
Mirjafary, Zohreh [1 ]
Taheri, Salman [1 ]
机构
[1] Sharif Univ Technol, Lab Organ Synth & Nat Prod, Dept Chem, POB 11155-9516, Tehran, Iran
[2] Payame Noor Univ, Dept Sci, Zanjan, Iran
关键词
Polycyclic heterocycles; tandem reaction; dibenzazocines; quinolinium salts; phenols; DIELS-ALDER REACTION; STRONG CH-ACIDS; NITROGEN-HETEROCYCLES; 3-COMPONENT REACTION; FACILE SYNTHESIS; RING-EXPANSION; SCAFFOLDS; ISOQUINOLINE; CHEMISTRY; SKELETONS;
D O I
10.3998/ark.5550190.0011.b09
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Dibenzazocines were prepared via tandem dinucleophilic addition of phenols to quinolinium salts in good yields. The procedure is efficient, simple and the substrates are easily available.
引用
收藏
页码:91 / 100
页数:10
相关论文
共 50 条
  • [41] Facile synthesis of N-alkyl-N′-arylimidazolium salts via addition of imidazoles to arynes
    Yoshida, H
    Sugiura, S
    Kunai, A
    ORGANIC LETTERS, 2002, 4 (16) : 2767 - 2769
  • [42] Selenochromanes via tandem homolytic addition/substitution chemistry
    Staples, Maree K.
    Schiesser, Carl H.
    CHEMICAL COMMUNICATIONS, 2010, 46 (04) : 565 - 567
  • [43] THE SYNTHESIS OF AZOCINE DERIVATIVES BY THE PHOTOCYCLO-ADDITION OF PHENOLS TO BENZONITRILE
    ALJALAL, N
    JOURNAL OF CHEMICAL RESEARCH-S, 1989, (04): : 110 - 111
  • [44] A NOVEL ONE-STEP SYNTHESIS OF QUINOLINIUM SALTS AND 4-QUINOLONES FROM FORMANILIDES
    METHCOHN, O
    TAYLOR, DL
    TETRAHEDRON LETTERS, 1993, 34 (22) : 3629 - 3632
  • [45] Synthesis of quaternary phosphonium salts from phosphorylated sterically hindered phenols
    V. V. Andriyashin
    Yu. V. Bakhtiyarova
    R. A. Cherkasov
    V. I. Galkin
    I. V. Galkina
    Russian Journal of Organic Chemistry, 2012, 48 : 1574 - 1575
  • [46] SYNTHESIS OF BENZOPYRYLIUM SALTS AND CHROMONES BY BIS-ACYLATION OF SOME PHENOLS
    DOROFEENKO, GN
    TKACHENK.VV
    KHIMIYA GETEROTSIKLICHESKIKH SOEDINENII, 1971, (12): : 1703 - +
  • [47] Synthesis of Aryl Alkyl Ethers by Alkylation of Phenols with Quaternary Ammonium Salts
    Maras, Nenad
    Polanc, Slovenko
    Kocevar, Marijan
    ACTA CHIMICA SLOVENICA, 2010, 57 (01) : 29 - 36
  • [48] Synthesis of Phenols from Aryl Ammonium Salts under Mild Conditions
    Ni, Pufan
    Yang, Lei
    Shen, Yi
    Zhang, Lei
    Ma, Yueyue
    Sun, Maolin
    Cheng, Ruihua
    Ye, Jinxing
    JOURNAL OF ORGANIC CHEMISTRY, 2022, 87 (19): : 12677 - 12687
  • [49] Synthesis of quaternary phosphonium salts from phosphorylated sterically hindered phenols
    Andriyashin, V. V.
    Bakhtiyarova, Yu. V.
    Cherkasov, R. A.
    Galkin, V. I.
    Galkina, I. V.
    RUSSIAN JOURNAL OF ORGANIC CHEMISTRY, 2012, 48 (12) : 1574 - 1575
  • [50] Enantioselective Total Synthesis of Cannabinoids via a Tandem Conjugate Addition/Enolate Alkylation Annulation with Ambiphilic Organoboronates
    Luo, Jirong
    May, Jeremy A.
    ORGANIC LETTERS, 2023, 25 (04) : 708 - 713