Synthesis of chalcones and flavanones using Julia-Kocienski olefination

被引：92
|
作者：
Kumar, Atul [1 ]
Sharma, Siddharth [1 ]
Tripathi, Vishwa Deepak [1 ]
Srivastava, Suman [1 ]
机构：
[1] CSIR, Cent Drug Res Inst, Med & Proc Chem Div, Lucknow 226001, Uttar Pradesh, India
来源：
TETRAHEDRON | 2010年 / 66卷 / 48期
关键词：
Chalcone; Flavanones; Julia-Kocienski olefination; HIGH-YIELD SYNTHESIS; 3,5-BIS(TRIFLUOROMETHYL)PHENYL SULFONES; ALPHA; BETA-UNSATURATED ESTERS; STEREOSELECTIVE-SYNTHESIS; TRANSFER HYDROGENATION; CARBONYL-COMPOUNDS; DERIVATIVES; STEREOCHEMISTRY; CARBANIONS; INHIBITORS;
D O I：
10.1016/j.tet.2010.09.089
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
A new application of Julia-Kocienski olefination for the synthesis of chalcones and flavanones has been described. 2-(Benzo[d]thiazol-2-ylsulfonyl)-1-phenylethanones have been developed as new reagents for direct Julia-Kocienski olefination with aldehydes in the presence of a base, afforded chalcones in good to excellent yields. Whereas, 2-(benzo[d]thiazol-2-ylsulfonyl)-1-(2-hydroxyphenyl)ethanone reacted with the aromatic aldehydes to furnish flavanones in good yields via one-pot intra-molecular cyclization. (C) 2010 Elsevier Ltd. All rights reserved.
引用
收藏
页码：9445 / 9449
页数：5
相关论文
共 50 条
  • [41] Novel Aromatic Fluoroolefins via Fluoro-Julia-Kocienski Olefination
    Allendoerfer, Nadine
    Es-Sayed, Mazen
    Nieger, Martin
    Braese, Stefan
    SYNTHESIS-STUTTGART, 2010, (20): : 3439 - 3448
  • [42] One-pot preparation of Julia-Kocienski sulfides and sulfones from alcohols
    Ando, Kaori
    Hattori, Junichiro
    TETRAHEDRON LETTERS, 2019, 60 (36)
  • [43] A New Julia-Kocienski Reagent for Convenient Access to the 2-Naphthylmethyl Vinyl Ethers
    Jeong, Myeonggyo
    Kang, Seongeun
    Torikai, Kohei
    Lee, Songyi
    Yun, Hwayoung
    ORGANIC PREPARATIONS AND PROCEDURES INTERNATIONAL, 2021, 53 (02) : 200 - 205
  • [44] Regiospecifically Fluorinated Polycyclic Aromatic Hydrocarbons via Julia-Kocienski Olefination and Oxidative Photocyclization. Effect of Fluorine Atom Substitution on Molecular Shape
    Banerjee, Shaibal
    Sinha, Saikat
    Pradhan, Padmanava
    Caruso, Alessio
    Liebowitz, Daniel
    Parrish, Damon
    Rossi, Miriam
    Zajc, Barbara
    JOURNAL OF ORGANIC CHEMISTRY, 2016, 81 (10): : 3983 - 3993
  • [45] Modified Julia-Kocienski Reaction Promoted by Means of m-NPT (Nitrophenyltetrazole) Sulfone
    Sakai, Yuki
    Ikeuchi, Kazutada
    Yamada, Yuji
    Wakimoto, Toshiyuki
    Kan, Toshiyuki
    SYNLETT, 2010, (05) : 827 - 829
  • [46] Asymmetric Synthesis of Chiral 1,3-Disubstituted Allylsilanes via Copper(I)-Catalyzed 1,4-Conjugate Silylation of α,β-Unsaturated Sulfones and Subsequent Julia-Kocienski Olefination
    Wang, Xian-Liang
    Yin, Xing-Hao
    Xiao, Jun-Zhao
    Jia, Xue-Shun
    Yin, Liang
    CHINESE JOURNAL OF CHEMISTRY, 2021, 39 (07) : 1916 - 1922
  • [47] Stereoselective Synthesis of Trisubstituted (Z)-Alkenes from Ketones via the Julia-Kocienski Olefination Using 1-Methyl- and 1-tert-Butyl-1H-tetrazol-5-yl Alkyl Sulfones
    Ando, Kaori
    Takama, Daiki
    ORGANIC LETTERS, 2020, 22 (17) : 6907 - 6910
  • [48] C-H-Alkenylation of Arenes in a One-Pot VNS - Julia-Kocienski Reaction
    Loska, Rafal
    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2018, 2018 (47) : 6649 - 6656
  • [49] Modified Julia-Kocienski Reagents for a Stereoselective Introduction of Trisubstituted Double Bonds: A Formal Total Synthesis of Limazepine E and Barmumycin
    Sakaine, Guna
    Smits, Gints
    JOURNAL OF ORGANIC CHEMISTRY, 2018, 83 (09): : 5323 - 5330
  • [50] SYNTHESIS OF PTEROSTILBENE BY JULIA OLEFINATION
    Peddikotla, Prabhakar
    Chittiboyina, Amar G.
    Khan, Ikhlas A.
    SYNTHETIC COMMUNICATIONS, 2013, 43 (23) : 3217 - 3223
12345