Synthesis of 2,3-dihydrobenzo[1,4]dioxins and -oxazins via a domino Wacker-Heck reaction

被引：0
|
作者：
Tietze, Lutz F. [1 ]
Wilckens, Kristina F. [1 ]
Yilmaz, Sinem [1 ]
Stecker, Florian [1 ]
Zinngrebe, Julia [1 ]
机构：
[1] Univ Gottingen, Inst Organ & Biomol Chem, D-37077 Gottingen, Germany
来源：
HETEROCYCLES | 2006年 / 70卷
关键词：
domio reacton; Wacker reaction; Heck reaction; palladium; heterocycle;
D O I：
暂无
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
An efficient and operationally simple domino Wacker-Heck reaction of allylic phenols and alpha,beta-unsaturated ketones as well as esters in the presence of catalytic amounts of Pd(TFA)(2) and an oxidant for the synthesis of 2,3-dihydrobcnzo[1,4]dioxins and 2,3-dihydrobenzo[1,4]oxazins is described. The necessary substrates are prepared by monoallylation of catechol derivatives and ortho-aminophenol.
引用
收藏
页码：309 / +
页数：12
相关论文
共 50 条
  • [1] Synthesis of 2,3-Dihydrobenzo[1,4]dithiin-Fused Porphyrins
    Jin, Guangnan
    Okujima, Tetsuo
    Hashimoto, Yusuke
    Yamada, Hiroko
    Uno, Hidemitsu
    Ono, Noboru
    PHOSPHORUS SULFUR AND SILICON AND THE RELATED ELEMENTS, 2010, 185 (5-6) : 1108 - 1116
  • [2] Enantioselective palladium-catalyzed total synthesis of vitamin E by employing a domino Wacker-Heck reaction
    Tietze, Lutz F.
    Stecker, Florian
    Zinngrebe, Julia
    Sommer, Konrad M.
    CHEMISTRY-A EUROPEAN JOURNAL, 2006, 12 (34) : 8770 - 8776
  • [3] Synthesis and glycogen phosphorylase inhibitor activity of 2,3-dihydrobenzo[1,4]dioxin derivatives
    Juhasz, Laszlo
    Docsa, Tibor
    Brunyaszki, Attila
    Gergely, Pal
    Antus, Sandor
    BIOORGANIC & MEDICINAL CHEMISTRY, 2007, 15 (12) : 4048 - 4056
  • [4] 2,4-DIARYL-2,3-DIHYDROBENZO[B][1,4]-THIAZEPINES
    ORLOV, VD
    KOLOS, NN
    RUZHITSKAYA, NN
    KHIMIYA GETEROTSIKLICHESKIKH SOEDINENII, 1983, (12): : 1638 - 1642
  • [5] Synthesis and antimicrobial activity of 2,4-diaryl-2,3-dihydrobenzo[b][1,4]thiazepines
    Mahendra Kumar
    Kailash Sharma
    Ankur Kumar Fogla
    Kanika Sharma
    Madhu Rathore
    Research on Chemical Intermediates, 2013, 39 : 2555 - 2564
  • [6] Synthesis and antimicrobial activity of 2,4-diaryl-2,3-dihydrobenzo[b][1,4]thiazepines
    Kumar, Mahendra
    Sharma, Kailash
    Fogla, Ankur Kumar
    Sharma, Kanika
    Rathore, Madhu
    RESEARCH ON CHEMICAL INTERMEDIATES, 2013, 39 (06) : 2555 - 2564
  • [7] 2,3-DIHYDROBENZO(F)-1,4-OXATHIEPIN AND DERIVATIVES
    KULKA, M
    CANADIAN JOURNAL OF CHEMISTRY-REVUE CANADIENNE DE CHIMIE, 1955, 33 (09): : 1442 - 1449
  • [8] Stereospecific synthesis of chiral tetrahydroquinoxaline, 2,3-dihydrobenzo[1,4]dioxin and 2,3-dihydro-naphtho[2,3-b][1,4]-dioxin derivatives
    Abdel-Jalil, RJ
    Shah, STA
    Khan, KM
    Voelter, W
    LETTERS IN ORGANIC CHEMISTRY, 2005, 2 (03) : 238 - 241
  • [9] Directed synthesis of fluorine containing 2,3-dihydrobenzo[b][1,4]oxathiine derivatives from polyfluoroarenes
    Politanskaya, Larisa
    Tretyakov, Evgeny
    JOURNAL OF FLUORINE CHEMISTRY, 2020, 236
  • [10] Synthesis and Evaluation of Novel 2,3-Dihydrobenzo[b][1,4]dioxin- and Indolealkylamine Derivatives as Potential Antidepressants
    Wang, Songlin
    Chen, Yin
    Liu, Xinghua
    Xu, Xiangqing
    Liu, Xin
    Liu, Bi-Feng
    Zhang, Guisen
    ARCHIV DER PHARMAZIE, 2014, 347 (01) : 32 - 41
12345