Tandem Demethylation/Annulation/Oxidation of 2,3-Bis(2-methoxyphenyl)-3-oxopropanals for One-Pot Construction of Coumestans

被引：8
|
作者：
Zhang, Jiefeng [1 ,2 ]
Qiu, Jiakun [1 ,2 ]
Xiao, Chunmei [1 ,2 ]
Yu, Lifang [1 ,2 ]
Yang, Fan [1 ,2 ]
Tang, Jie [1 ,2 ]
机构：
[1] East China Normal Univ, Shanghai Engn Res Ctr Mol Therapeut & New Drug De, 3663 North Zhongshan Rd, Shanghai 200062, Peoples R China
[2] East China Normal Univ, Shanghai Key Lab Green Chem & Chem Proc, Sch Chem & Mol Engn, 3663 North Zhongshan Rd, Shanghai 200062, Peoples R China
来源：
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY | 2016年 / 2016卷 / 20期
关键词：
Domino reactions; Annulation; Oxidation; Tautomerism; Oxygen heterocycles; MEINWALD REARRANGEMENT; WEDELOLACTONE; DERIVATIVES; CYCLIZATION; ACTIVATION; EPOXIDES;
D O I：
10.1002/ejoc.201600122
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
A convenient and practical approach to coumestans has been successfully developed by using a one-pot tandem demethylation/annulation/oxidation reaction sequence that employs easily accessible 2,3-bis(2-methoxyphenyl)-3-oxo-propanals as the starting material. This synthetic protocol provided a variety of coumestan derivatives in good to excellent yields under mild conditions. The exploration of biologically active coumestan compounds is a potential application of this synthetic method.
引用
收藏
页码：3380 / 3385
页数：6
相关论文
共 50 条
  • [1] 2,3-Bis(2-methoxyphenyl)tetrazolium-5-thiolate-acetone-dichloromethane (1/0.4/0.1)
    von Eschwege, Karel G.
    Muller, Alfred
    ACTA CRYSTALLOGRAPHICA SECTION E-STRUCTURE REPORTS ONLINE, 2009, 65 : O2 - U1267
  • [2] (E) AND (Z)-2,3-BIS(2-METHOXYPHENYL)-2-BUTENE, C18H20O2
    FRONCZEK, FR
    OLIVER, MA
    GANDOUR, RD
    ACTA CRYSTALLOGRAPHICA SECTION C-CRYSTAL STRUCTURE COMMUNICATIONS, 1984, 40 (MAR) : 504 - 506
  • [3] A facile, one-pot preparation of 2,3-dimethyl-2,3-bis (2-oxazolinyl) butane and its structure characterization.
    Wang, B
    Swanson, DR
    Knoerr, SM
    Milco, LA
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 1997, 214 : 323 - ORGN
  • [4] One-Pot Tandem Protocol for the Synthesis of 1,3-Bis(β-aminoacrylate)-Substituted 2-Mercaptoimidazole Scaffolds
    Luo, Jian
    Chen, Guo-Shu
    Chen, Shu-Jie
    Li, Zhao-Dong
    Zhao, Yu-Lei
    Liu, Yun-Lin
    ADVANCED SYNTHESIS & CATALYSIS, 2020, 362 (17) : 3635 - 3643
  • [5] One-pot synthesis of 1,3-bis(cytisinyl)propan-2-ol
    D. V. Shishkin
    N. Z. Baibulatova
    V. A. Dokichev
    Russian Journal of Organic Chemistry, 2009, 45 : 1879 - 1880
  • [6] One-pot synthesis of 1,3-bis(cytisinyl)propan-2-ol
    Shishkin, D. V.
    Baibulatova, N. Z.
    Dokichev, V. A.
    RUSSIAN JOURNAL OF ORGANIC CHEMISTRY, 2009, 45 (12) : 1879 - 1880
  • [7] One-Pot Synthesis of Azobenzene Derivatives by Oxidation of 2,3-Dihydrobenzothiadiazines
    Cannazza, Giuseppe
    Perrone, Serena
    Rosato, Francesca
    D'Accolti, Lucia
    Parenti, Carlo
    Troisi, Luigino
    SYNTHESIS-STUTTGART, 2014, 46 (07): : 962 - 966
  • [8] 2,3-bis(5-alkyl-2-thiono-1,3,5-thiadiazin-3-yl) propionic acid:: One-pot Domino Synthesis and antimicrobial activity
    El Bialy, SAA
    Abdelal, AM
    Ei-Shorbagi, AN
    Kheira, SMM
    ARCHIV DER PHARMAZIE, 2005, 338 (01) : 38 - 43
  • [9] 2,4-Bis(2-methoxyphenyl)-3-azabicyclo[3.3.1]nonan-9-one
    Parthiban, P.
    Ramkumar, V.
    Kim, Min Sung
    Son, Se Mo
    Jeong, Yeon Tae
    ACTA CRYSTALLOGRAPHICA SECTION E-STRUCTURE REPORTS ONLINE, 2009, 65 : O1383 - U2793
  • [10] One-pot electrosynthesis of 2,3-bis(spiro-2-indanyl-1,3-dione)indeno[1,2-b]furan-4-one
    Horcajada, Roberto
    Batanero, Belen
    Barba, Fructuoso
    Martin, Avelino
    TETRAHEDRON LETTERS, 2007, 48 (37) : 6437 - 6441
12345