OXIDATION REACTIONS OF 2'-FUNCTIONALIZED 3-ARYLTETRAHYDROQUINOLINES AND 3,4-DIHYDROISOQUINOLINES

被引：13
|
作者：
SOTOMAYOR, N [1 ]
DOMINGUEZ, E [1 ]
LETE, E [1 ]
机构：
[1] UNIV BASQUE COUNTRY, FAC CIENCIAS, DEPT QUIM ORGAN, E-48080 BILBAO, SPAIN
来源：
TETRAHEDRON | 1995年 / 51卷 / 46期
关键词：
D O I：
10.1016/0040-4020(95)00827-U
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
Several 2'-functionalized 3-arylisoquinolines in different oxidation stages have been prepared. Fremy's salt or I-2/NaAcO oxidation of 2'-functionalized 3-aryltetrahydroisoquinolines always stops at the 3,4-dihydroisquinoline stage; however, better yields and shorter reaction Limes are obtained with iodine. Air/KOH/DMSO oxidation of 3,4-dihydroisoquinolines furnished the aromatic derivatives with concomitant cleavage of the TBDPS group. While 3-arylisoquinolin-1-(2H)-ones are obtained by air oxidation of 3,4-dihydroisquinolinium salts, the use of DDQ in dioxane resulted in a selective dehydrogenation to the corresponding N-substituted isoquinolinium salts.
引用
收藏
页码：12721 / 12730
页数：10
相关论文
共 50 条
  • [31] Symmetrical and unsymmetrical bis-1,1′-(3,4-dihydroisoquinolines)
    Glushkov V.A.
    Karmanov V.I.
    Shklyaev Yu.V.
    Chemistry of Heterocyclic Compounds, 2005, 41 (4) : 475 - 480
  • [32] Synthesis of 3,3-dialkyl-1-(3-pyridyl)-3,4-dihydroisoquinolines
    Polygalova N.N.
    Mikhailovskii A.G.
    Udodov V.V.
    Mikhalev A.I.
    Vakhrin M.I.
    Chemistry of Heterocyclic Compounds, 2007, 43 (08) : 1024 - 1028
  • [33] INTERACTION OF DICHLOROCARBENE WITH SUBSTITUTED 3,4-DIHYDROISOQUINOLINES AND 1-METHYLENE-1,2,3,4-TETRAHYDROISOQUINOLINES
    KHLEBNIKOV, AF
    KOSTIKOV, RR
    SHKLYAEV, VS
    ALEKSANDROV, BB
    DORMIDONTOV, MY
    KHIMIYA GETEROTSIKLICHESKIKH SOEDINENII, 1990, (08): : 1086 - 1091
  • [34] 3,4-DIHYDROISOQUINOLINES .3. 1-SUBSTITUTED 5,6-DIHYDROPYRROLO[2,1-A]ISOQUINOLINES BY BASE-CATALYZED RING TRANSFORMATION OF 1-FURYL-3,4-DIHYDROISOQUINOLINES
    LOSEL, W
    CHEMISCHE BERICHTE-RECUEIL, 1988, 121 (03): : 547 - 550
  • [35] Thiocarbamoylation of 1,3,3-trimethyl-3,4-dihydroisoquinolines with benzoyl isothiocyanate
    A. G. Mikhailovskii
    A. S. Yusov
    O. V. Gashkova
    Russian Journal of Organic Chemistry, 2015, 51 : 1818 - 1819
  • [36] Iron-catalyzed stereoselective allylboration of 3,4-dihydroisoquinolines with potassium allyltrifluoroborates
    Fang, Yong
    Hu, Xiaoling
    Shi, Zhuangzhuang
    Zhao, Xu
    Gopireddy, Raveendra Reddy
    Luo, Yunfei
    Synthesis (Germany), 2021, 53 (19) : 3564 - 3572
  • [37] Iron-Catalyzed Stereoselective Allylboration of 3,4-Dihydroisoquinolines with Potassium Allyltrifluoroborates
    Fang, Yong
    Hu, Xiaoling
    Shi, Zhuangzhuang
    Zhao, Xu
    Gopireddy, Raveendra Reddy
    Luo, Yunfei
    SYNTHESIS-STUTTGART, 2021, 53 (19): : 3564 - 3572
  • [38] Domino Reactions of 1-Aroyl-3,4-dihydroisoquinolines with α,β-Unsaturated Aldehydes
    Matveeva, Maria D.
    Borisova, Tatiana N.
    Titov, Alexander A.
    Anikina, Lada V.
    Dyachenko, Svetlana V.
    Astakhov, Grigorii S.
    Varlamov, Alexey V.
    Voskressensky, Leonid G.
    SYNTHESIS-STUTTGART, 2017, 49 (23): : 5251 - 5257
  • [39] PARTIAL O-DEMETHYLATION OF AROMATIC-SUBSTITUTED 3,4-DIHYDROISOQUINOLINES
    BROSSI, A
    TEITEL, S
    HELVETICA CHIMICA ACTA, 1970, 53 (07) : 1779 - &
  • [40] Thiocarbamoylation of 1,3,3-trimethyl-3,4-dihydroisoquinolines with benzoyl isothiocyanate
    Mikhailovskii, A. G.
    Yusov, A. S.
    Gashkova, O. V.
    RUSSIAN JOURNAL OF ORGANIC CHEMISTRY, 2015, 51 (12) : 1818 - 1819
12345