Base-catalyzed condensation of 2-hydroxybenzaldehydes with α,β-unsaturated aldehydes -: Scope and limitations

被引：70
|
作者：
Lesch, B
Toräng, J
Vanderheiden, S
Bräse, S
机构：
[1] Univ Karlsruhe, Inst Organ Chem, TH, D-76131 Karlsruhe, Germany
[2] Univ Bonn, Inst Organ Chem, D-53121 Bonn, Germany
来源：
ADVANCED SYNTHESIS & CATALYSIS | 2005年 / 347卷 / 04期
关键词：
gamma-aldol reaction; enols; enones; nucleophilic addition; oxygen heterocycles;
D O I：
10.1002/adsc.200404239
中图分类号：
O69 [应用化学];
学科分类号：
081704 ;
摘要：
The base-catalyzed condensation of alpha,beta-unsaturated carbonyl compounds with 2-hydroxybenzaldehydes yielding tetrahydroxanthones and dihydrobenzopyrans has been investigated. A novel access to highly functionalized dihydrobenzopyrans via a mild generation of the dienol of senecialdehyde and subsequent conjugated aldol reaction has been reported.
引用
收藏
页码：555 / 562
页数：8
相关论文
共 50 条
  • [21] Preparation of α-labeled aldehydes by base-catalyzed exchange reactions
    Ariza, Xavier
    Asins, Guillermina
    Garcia, Jordi
    Hegardt, Fausto G.
    Makowski, Kamil
    Serra, Dolors
    Velasco, Javier
    JOURNAL OF LABELLED COMPOUNDS & RADIOPHARMACEUTICALS, 2010, 53 (7-8): : 556 - 558
  • [22] REINVESTIGATION OF BASE-CATALYZED CONDENSATION OF ETHYL ALPHA,ALPHA-DICHLOROACETOACETATE WITH ALDEHYDES - A NEW SYNTHESIS OF (+/-)-DISPARLURE
    TSUBOI, S
    FURUTANI, H
    TAKEDA, A
    KAWAZOE, K
    SATO, S
    BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN, 1987, 60 (07) : 2475 - 2479
  • [23] Scope and limitations of the base-catalyzed phospha-peterson P=C bond-forming reaction
    Yam, Mandy
    Chong, Jonathan H.
    Tsang, Chi-Wing
    Patrick, Brian O.
    Lam, Anita E.
    Gates, Derek P.
    INORGANIC CHEMISTRY, 2006, 45 (13) : 5225 - 5234
  • [24] THE KINETICS OF THE BASE-CATALYZED CONDENSATION OF BENZALDEHYDE WITH PHENACYL CHLORIDE
    BALLESTER, M
    BARTLETT, PD
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1953, 75 (09) : 2042 - 2043
  • [25] BASE-CATALYZED CONDENSATION OF ALPHA-HALOALDEHYDES WITH DICHLOROACETATES
    TAKEDA, A
    TSUBOI, S
    WADA, S
    KATO, H
    BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN, 1972, 45 (04) : 1217 - +
  • [26] SECONDARY REACTIONS OF THE BASE-CATALYZED ALDOL CONDENSATION OF ACETONE
    LIPPERT, S
    BAUMANN, W
    THOMKE, K
    JOURNAL OF MOLECULAR CATALYSIS, 1991, 69 (02): : 199 - 214
  • [27] KINETICS OF BASE-CATALYZED SELF-CONDENSATION OF CHLOROACETONE
    AWAD, WI
    WAHHAB, SMA
    AWAD, BM
    GUIRGUIS, NR
    WASSEF, WN
    INDIAN JOURNAL OF CHEMISTRY SECTION B-ORGANIC CHEMISTRY INCLUDING MEDICINAL CHEMISTRY, 1977, 15 (08): : 737 - 739
  • [28] ANALYSIS OF BASE-CATALYZED PHENOL-EPICHLOROHYDRIN CONDENSATION
    BRODE, GL
    WYNSTRA, J
    JOURNAL OF POLYMER SCIENCE PART A-1-POLYMER CHEMISTRY, 1966, 4 (5PA1): : 1045 - &
  • [29] EFFECT OF PRESSURE AND TEMPERATURE ON BASE-CATALYZED CONDENSATION OF CYCLOHEXANONE
    MORIYOSHI, T
    MIKAMI, K
    REVIEW OF PHYSICAL CHEMISTRY OF JAPAN, 1968, 38 (01): : 50 - +
  • [30] Phosphazene base-catalyzed condensation of trimethylsilylacetate with carbonyl compounds
    Kobayashi, Koji
    Ueno, Masahiro
    Kondo, Yoshinori
    CHEMICAL COMMUNICATIONS, 2006, (29) : 3128 - 3130
12345