A one-pot three-step multicomponent synthesis of functionalized allyl dithiocarbamates using Baylis-Hillman reaction

被引:6
|
作者
Ziyaei Halimehjani, Azim [1 ]
Lotfi Nosood, Yazdanbakhsh [1 ]
Sharifi, Marzieh [1 ]
机构
[1] Kharazmi Univ, Fac Chem, Tehran 15614, Iran
关键词
Allyl dithiocarbamates; Baylis-Hillman reaction; carbon disulfide; multicomponent reactions; EFFICIENT; DERIVATIVES; ACCESS;
D O I
10.1080/00397911.2020.1725974
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A one-pot, pseudo five-component, highly diastereoselective, and mild procedure for the synthesis of functionalized allyl dithiocarbamates is developed. The Baylis-Hillman (BH) reaction of aromatic (heteroaromatic) aldehydes and activated alkenes using DABCO, followed by acetylation of BH adducts with acetic anhydride in the presence of a catalytic amount of DMAP, and nucleophilic substitution reaction by in situ prepared dithiocarbamates from amines and CS2 are three steps of this protocol.
引用
收藏
页码:966 / 972
页数:7
相关论文
共 50 条
  • [11] A facile and stereoselective synthesis of unsymmetrical diallylsulfides via indium-promoted one-pot reaction of Baylis-Hillman acetates, sodium thiosulfate, and allyl bromide
    Liu, YK
    Xu, XS
    Zheng, H
    Xu, DQ
    Xu, ZY
    Zhang, YM
    SYNLETT, 2006, (04) : 571 - 574
  • [12] Asymmetric synthesis of chiral β-iodo Baylis-Hillman esters using MgI2 as promoter via a one-pot three-component reaction
    Wei, HX
    Chen, DJ
    Xu, X
    Li, GG
    Paré, PW
    TETRAHEDRON-ASYMMETRY, 2003, 14 (08) : 971 - 974
  • [13] 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
  • [14] Baylis-Hillman Reaction as a Versatile Platform for the Synthesis of Diverse Functionalized Polymers by Chain and Step Polymerization
    Peng, Chao
    Joy, Abraham
    MACROMOLECULES, 2014, 47 (04) : 1258 - 1268
  • [15] Baylis-Hillman acetates in organic synthesis: convenient one-pot synthesis of α-carboline framework - a concise synthesis of neocryptolepine
    Basavaiah, Deevi
    Reddy, Daggula Mallikarjuna
    ORGANIC & BIOMOLECULAR CHEMISTRY, 2012, 10 (44) : 8774 - 8777
  • [16] The first one-pot oxidative Michael reaction of Baylis-Hillman adducts with indoles promoted by iodoxybenzoic acid
    Yadav, J. S.
    Reddy, B. V. Subba
    Singh, Ashutosh Pratap
    Basak, A. K.
    TETRAHEDRON LETTERS, 2007, 48 (24) : 4169 - 4172
  • [17] Z/E stereoselective synthesis of β-bromo Baylis-Hillman ketones using MgBr2 as promoter via a one-pot three-component reaction
    Wei, HX
    Jasoni, RL
    Hu, JL
    Li, GG
    Paré, PW
    TETRAHEDRON, 2004, 60 (45) : 10233 - 10237
  • [18] Baylis-Hillman reaction as a versatile platform for the synthesis of densely functionalized polymers
    Joy, Abraham
    Peng, Chao
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2015, 249
  • [19] Baylis-Hillman chemistry: a one pot cross-coupling/allylboration reaction
    Kabalka, GW
    Venkataiah, B
    Dong, G
    TETRAHEDRON LETTERS, 2005, 46 (24) : 4209 - 4211
  • [20] The Baylis-Hillman reaction:: An expedient synthesis of (Z)-keto allyl bromides and chlorides
    Basavaiah, D
    Hyma, RS
    Padmaja, K
    Krishnamacharyulu, M
    TETRAHEDRON, 1999, 55 (22) : 6971 - 6976