An efficient catalyst-free one-pot synthesis of primary amides from the aldehydes of the Baylis-Hillman reaction

被引:13
|
作者
Reddy, Thatikonda Narendar [1 ,2 ]
Raktani, Bikshapathi [1 ,2 ]
Perla, Ramesh [3 ]
Ravinder, Mettu [1 ,2 ]
Vaidya, Jayathirtha Rao [1 ,2 ]
Babu, N. Jagadeesh [4 ]
机构
[1] Indian Inst Chem Technol, CSIR, Crop Protect Chem Div, Uppal Rd, Hyderabad 500007, Andhra Prades, India
[2] Indian Inst Chem Technol, CSIR, AcSIR, Uppal Rd, Hyderabad 500007, Andhra Prades, India
[3] Indian Inst Chem Technol, CSIR, Nat Prod Chem Div, Hyderabad 500007, Andhra Prades, India
[4] Indian Inst Chem Technol, CSIR, Ctr Xray Crystallog, Hyderabad 500007, Andhra Prades, India
关键词
KNOEVENAGEL CONDENSATION; ALPHA; BETA-UNSATURATED AMIDES; CONVENIENT SYNTHESIS; OXIDATIVE AMIDATION; AEROBIC OXIDATION; DIRECT CONVERSION; GREEN PROCEDURE; MILD AMIDATION; N-FORMYLATION; IONIC LIQUID;
D O I
10.1039/c7nj01965c
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Herein, a facile and efficient method for the preparation of allyl amides from the aldehyde of Baylis-Hillman adducts has been developed using a hydroxylamine/methanol system under a catalyst-free condition. The effects of solvents and temperature on the reaction and substituents on the phenyl ring have been examined. This method is best demonstrated by its advantages such as operational simplicity, moderate to excellent yields, short reaction time, and simple reaction procedure. Most importantly, the reaction proceeds smoothly in the absence of a catalyst and an external oxidant.
引用
收藏
页码:9203 / 9209
页数:7
相关论文
共 50 条
  • [1] One-pot sequential Baylis-Hillman and Michael reactions
    Wang, WG
    Yu, M
    TETRAHEDRON LETTERS, 2004, 45 (38) : 7141 - 7143
  • [2] One-pot synthesis of new type aza- Baylis-Hillman adducts from chlorovinyl aldehydes under solvent-free condition
    Zhong, Weihui
    Chen, Yanhui
    Wang, Guan
    JOURNAL OF CHEMICAL RESEARCH, 2010, (01) : 44 - 49
  • [3] Ketones as electrophiles in two component Baylis-Hillman reaction: a facile one-pot synthesis of substituted indolizines
    Basavaiah, Deevi
    Veeraraghavaiah, Gorre
    Badsara, Satpal Singh
    ORGANIC & BIOMOLECULAR CHEMISTRY, 2014, 12 (10) : 1551 - 1555
  • [4] Applications of Baylis-Hillman acetates:: one-pot, facile and convenient synthesis of substituted γ-lactams
    Basavaiah, D
    Rao, JS
    TETRAHEDRON LETTERS, 2004, 45 (08) : 1621 - 1625
  • [5] Selenonium ionic liquid as efficient catalyst for the Baylis-Hillman reaction
    Lenardao, Eder J.
    Feijo, Josiane de Oliveira
    Thurow, Samuel
    Perin, Gelson
    Jacob, Raquel G.
    Silveira, Claudio C.
    TETRAHEDRON LETTERS, 2009, 50 (37) : 5215 - 5217
  • [6] A one-pot three-step multicomponent synthesis of functionalized allyl dithiocarbamates using Baylis-Hillman reaction
    Ziyaei Halimehjani, Azim
    Lotfi Nosood, Yazdanbakhsh
    Sharifi, Marzieh
    SYNTHETIC COMMUNICATIONS, 2020, 50 (07) : 966 - 972
  • [7] First example of electrophile induced Baylis-Hillman reaction: a novel facile one-pot synthesis of indolizine derivatives
    Basavaiah, D
    Rao, AJ
    CHEMICAL COMMUNICATIONS, 2003, (05) : 604 - 605
  • [8] Fast, microwave-promoted one-pot synthesis of bicyclic pyrimidones from Baylis-Hillman adducts
    Liu, Yongliang
    Wan, Kun
    Wang, Zengxue
    JOURNAL OF CHEMICAL RESEARCH, 2015, (02) : 63 - 66
  • [9] A one-pot synthesis of primary amides from aldoximes or aldehydes in water in the presence of a supported rhodium catalyst
    Fujiwara, Hiroshi
    Ogasawara, Yoshiyuki
    Yamaguchi, Kazuya
    Mizuno, Noritaka
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2007, 46 (27) : 5202 - 5205
  • [10] Applications of Baylis-Hillman adducts: a simple, convenient, and one-pot synthesis of 3-benzoylquinolines
    Basavaiah, D
    Reddy, RJ
    Rao, JS
    TETRAHEDRON LETTERS, 2006, 47 (01) : 73 - 77