Ga(OTf)3-mediated synthesis of substituted benzofurans

被引：11
|
作者：
Wang, Heui-Sin [1 ]
Chan, Chieh-Kai [1 ]
Chang, Meng-Yang [1 ]
机构：
[1] Kaohsiung Med Univ, Dept Med & Appl Chem, Kaohsiung 807, Taiwan
来源：
TETRAHEDRON | 2016年 / 72卷 / 33期
关键词：
Ga(OTf)(3); Benzofurans; Cyclodehydration; Scholl annulation; ONE-POT SYNTHESIS; GALLIUM(III) TRIFLATE; ORGANIC-SYNTHESIS; 2,3-DISUBSTITUTED BENZOFURANS; ELECTROPHILIC CYCLIZATION; STRAIGHTFORWARD SYNTHESIS; OXIDATIVE CYCLIZATION; SELECTIVE SYNTHESIS; TERMINAL ALKYNES; ALPHA-ARYLATION;
D O I：
10.1016/j.tet.2016.07.007
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
A synthetic procedure, for the synthesis of a series of functionalized benzofurans 3-5 and benzonaphthofurans 6, starting from intermolecular O-alkylation of alpha-bromoaryl ketones 2 with potassium oxygenated phenoxides 1 followed by Ga(OTf)(3)-catalyzed direct intramolecular cyclodehydration of the resulting alpha-aryloxyaryl ketones, has been developed. The use of various metal triflates was investigated for a facile approach and efficient transformation. Pentacyclic benzophenanthrofurans 7 were prepared via photolytic annulations of 5. (C) 2016 Elsevier Ltd. All rights reserved.
引用
收藏
页码：5132 / 5141
页数：10
相关论文
共 50 条
  • [41] A convenient synthesis of 2-substituted benzofurans from salicylaldehydes
    Reddy, Swetha
    Thadkapally, Srinivas
    Mamidyala, Mounika
    Nanubolu, Jagadeesh Babu
    Menon, Rajeev S.
    RSC ADVANCES, 2015, 5 (11) : 8199 - 8204
  • [42] SYNTHESIS AND PHARMACOLOGICAL PROPERTIES OF BENZOFURANS SUBSTITUTED IN 2 BY AN ACIDIC GROUP
    AUROZO, A
    FAURE, R
    MATTIODA, G
    EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, 1975, 10 (02) : 182 - 186
  • [43] A facile approach to the synthesis of chiral 2-substituted benzofurans
    De Luca, Lidia
    Giacomelli, Giampaolo
    Nieddu, Giammario
    JOURNAL OF ORGANIC CHEMISTRY, 2007, 72 (10): : 3955 - 3957
  • [44] Integrin αvβ3-mediated activation of apoptosis
    Brassard, DL
    Maxwell, E
    Malkowski, M
    Nagabhushan, TL
    Kumar, CC
    Armstrong, L
    EXPERIMENTAL CELL RESEARCH, 1999, 251 (01) : 33 - 45
  • [45] Expanding the scope of Mn(OAc)3-mediated cyclizations:: Synthesis of the tetracyclic core of tronocarpine
    Magolan, Jakob
    Kerr, Michael A.
    ORGANIC LETTERS, 2006, 8 (20) : 4561 - 4564
  • [46] Opsin 3-Mediated Regulation of Skin Pigmentation
    Olinski, Lauren E.
    Ozdeslik, Rana N.
    Oancea, Elena
    JOURNAL OF GENERAL PHYSIOLOGY, 2017, 149 (09): : 11A - 12A
  • [47] AlkB homolog 3-mediated tRNA demethylation promotes protein synthesis in cancer cells
    Ueda, Yuko
    Ooshio, Ikumi
    Fusamae, Yasuyuki
    Kitae, Kaori
    Kawaguchi, Megumi
    Jingushi, Kentaro
    Hase, Hiroaki
    Harada, Kazuo
    Hirata, Kazumasa
    Tsujikawa, Kazutake
    SCIENTIFIC REPORTS, 2017, 7
  • [48] AlkB homolog 3-mediated tRNA demethylation promotes protein synthesis in cancer cells
    Yuko Ueda
    Ikumi Ooshio
    Yasuyuki Fusamae
    Kaori Kitae
    Megumi Kawaguchi
    Kentaro Jingushi
    Hiroaki Hase
    Kazuo Harada
    Kazumasa Hirata
    Kazutake Tsujikawa
    Scientific Reports, 7
  • [49] Synthesis of novel 6-unsubstituted 2-aminodihydropyrimidines by Sc(OTf)3-mediated amination and their antiproliferative effect on HL-60 cells (vol 65, 152760, 2021)
    Nishimura, Yoshio
    Kikuchi, Hidetomo
    Kubo, Takanori
    Nakakita, Ibuki
    Oguni, Mari
    Ohta, Misaki
    Arai, Rie
    Yuan, Bo
    Sunaga, Katsuyoshi
    Cho, Hidetsura
    TETRAHEDRON LETTERS, 2021, 76
  • [50] Reactions of alkoxyaryloxycarbenes with tethered triple bonds: a new synthesis of substituted benzofurans
    Kassam, K
    Venneri, PC
    Warkentin, J
    CANADIAN JOURNAL OF CHEMISTRY-REVUE CANADIENNE DE CHIMIE, 1997, 75 (09): : 1256 - 1263
12345