A Weinreb Amide Based Building Block for Convenient Access to β,β-Diarylacroleins: Synthesis of 3-Arylindanones

被引：9
作者：
Tiwari, Praveen Kumar [1 ]
Aidhen, Indrapal Singh [1 ]
机构：
[1] Indian Inst Technol, Dept Chem, Madras 600036, Tamil Nadu, India
来源：
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY | 2016年 / 2016卷 / 15期
关键词：
Synthetic methods; C3 Building blocks; Amides; Grignard reaction; HECK REACTION; ASYMMETRIC-SYNTHESIS; CARBOXYLIC-ACIDS; (+)-INDATRALINE; HYDROGENATION; DERIVATIVES; ANTAGONISTS; ALDEHYDES; INDANONES; AGONISTS;
D O I：
10.1002/ejoc.201600193
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
Towards the synthesis of symmetrical and unsymmetrical beta,beta-diarylacroleins for assembling diarylmethine fragments present in biologically important molecules, we have developed a new Weinreb amide (WA) based building block, derived from propiolic acid. The WA functionality present in this compound allowed the sequential addition of various arylmagnesium bromide reagents in a controlled manner. The developed methodology for the access to beta,beta-diarylacroleins has been utilised for the synthesis of biologically important 3-arylindanone molecules.
引用
收藏
页码：2637 / 2646
页数：10
相关论文
共 50 条
  • [21] Synthesis of antimalarial amide analogues based on the plant serrulatane diterpenoid 3,7,8-trihydroxyserrulat-14-en-19-oic acid
    Kumar, Rohitesh
    Duffy, Sandra
    Avery, Vicky M.
    Davis, Rohan A.
    BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2017, 27 (17) : 4091 - 4095
  • [22] Concise synthesis of ω-fluoroalkylated ketoesters. A building block for the synthesis of six-, seven-, and eight-membered fluoroalkyl substituted 1,2-diaza-3-one heterocycles
    Wan, Wen
    Hou, Jie
    Jiang, Haizhen
    Wang, Yangli
    Zhu, Shizheng
    Deng, Hongmei
    Hao, Jian
    TETRAHEDRON, 2009, 65 (21) : 4212 - 4219
  • [23] Electrogenerated Low Band Gap Polymers Based on the 3-Cyano-4-methoxythiophene Building Block
    Hergue, Noemie
    Mallet, Charlotte
    Frere, Pierre
    Allain, Magali
    Roncali, Jean
    MACROMOLECULES, 2009, 42 (15) : 5593 - 5599
  • [24] Synthesis of betulin dioleate epoxide as a bio-based building block for epoxy resin formulations with modified rapeseed oil
    Buss, Rinalds
    Platnieks, Oskars
    Kumpins, Viktors
    Mierina, Inese
    Turks, Maris
    Leitans, Armands
    Kirpluks, Mikelis
    Gaidukovs, Sergejs
    REACTIVE & FUNCTIONAL POLYMERS, 2025, 214
  • [25] Synthesis and characterization of poly(ester amide)-based materials for 3D printing of tissue engineering scaffolds
    dos Santos, Patricia
    Alves, Beatriz
    Inocencio, Sara
    Nunes, Pedro
    Richardson, Stephen M.
    Gloria, Antonio
    Serra, Armenio
    Fonseca, Ana Clotilde
    Domingos, Marco
    JOURNAL OF MATERIALS CHEMISTRY B, 2025, 13 (09) : 3049 - 3066
  • [26] 2,3,3,3-Tetrafluoropropene (HFO-1234yf) as a CF3-Building Block: Synthesis of Enol Ethers and Vinyl Sulfides
    Murray, Ben J.
    Ball, Ellis D.
    Harsanyi, Antal
    Sandford, Graham
    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2019, 2019 (47) : 7666 - 7672
  • [27] Facile and Efficient Synthesis of (R)-4-(Benzyloxy)-3-methylbutanenitrile: Toward Developing a Versatile Chiral Building Block
    Song Zijie
    Shi Yong
    Jin Ronghua
    Lin Jingrong
    Tian Weisheng
    CHINESE JOURNAL OF CHEMISTRY, 2012, 30 (10) : 2595 - 2597
  • [28] DIMENTHOXYPHOSPHORYLIMINO-3,3,3-TRIFLUOROPROPIONATE AS A NOVEL CHIRAL BUILDING BLOCK IN ASYMMETRIC SYNTHESIS OF FLUORINATED α-AMINO ACIDS DERIVATIVES
    Rassukana, Yuliya V.
    Khomutnyk, Yaroslav Y.
    Synytsya, Anatoly D.
    Onys'ko, Petro P.
    PHOSPHORUS SULFUR AND SILICON AND THE RELATED ELEMENTS, 2011, 186 (04) : 718 - 720
  • [29] A convenient access to (3S)-3-(triisopropylsilyl)oxy-1-pyrroline N-oxide, a useful intermediate for polyfunctionalized enantiopure indolizidine and pyrrolizidine synthesis
    Goti, A
    Cacciarini, M
    Cardona, F
    Brandi, A
    TETRAHEDRON LETTERS, 1999, 40 (14) : 2853 - 2856
  • [30] Allylation of (R)-2,3-O-Cyclohexylideneglyceraldehyde with Methyl 3-(Bromomethyl)but-3-enoate. Methyl 3-{(2S)-2-[(2R)-1,4-Dioxaspiro[4.5]dec-2-yl]-2-hydroxyethyl}but-3-enoate as a Convenient Universal Building Block for the Synthesis of Key Fragments of Bioactive Compounds
    Mineeva, I., V
    RUSSIAN JOURNAL OF ORGANIC CHEMISTRY, 2019, 55 (08) : 1112 - 1123
12345