New efficient synthesis of trisubstituted imidazolidine-2-thiones and thiazoles via vinyliminophosphoranes

被引：33
|
作者：
Xie, Hai [1 ,2 ]
Liu, Jian-Chao [1 ]
Wu, Lei [1 ]
Ding, Ming-Wu [1 ]
机构：
[1] Cent China Normal Univ, Key Lab Pesticide & Chem Biol, Minist Educ, Wuhan 430079, Peoples R China
[2] Shanxi Datong Univ, Coll Chem & Chem Engn, Datong 037009, Shanxi, Peoples R China
来源：
TETRAHEDRON | 2012年 / 68卷 / 38期
基金：
中国国家自然科学基金;
关键词：
BIOLOGICAL EVALUATION; UNEXPECTED SYNTHESIS; FACILE SYNTHESIS; INHIBITORS; IMIDAZOLES; DERIVATIVES; ENAZIDES; DESIGN; SERIES;
D O I：
10.1016/j.tet.2012.07.002
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
Isothiocyanate 6, obtained from vinyliminophosphorane 4 with CS2, reacted with various aliphatic primary amines to afford directly the 1,4,5-trisubstituted imidazolidine-2-thiones 5. However, the reaction of isothiocyanate 6 with aliphatic secondary amines provided 2,4,5-trisubstituted thiazoles 10 in good yields. (C) 2012 Elsevier Ltd. All rights reserved.
引用
收藏
页码：7984 / 7990
页数：7
相关论文
共 50 条
  • [1] SYNTHESIS OF IMIDAZOLINE-2-THIONES AND IMIDAZOLIDINE-2-THIONES
    FERNANDEZBOLANO.J
    GOMEZ, JG
    MENENDEZ.M
    GARCIAGONZALEZ, FG
    TETRAHEDRON, 1963, 19 (12) : 1883 - &
  • [2] Synthesis and structure of some imidazolidine-2-thiones
    T. S. Zhivotova
    A. M. Gazaliev
    S. D. Fazylov
    Z. K. Aitpaeva
    D. M. Turdybekov
    Russian Journal of Organic Chemistry, 2006, 42 : 448 - 450
  • [3] Synthesis and structure of some imidazolidine-2-thiones
    Zhivotova, TS
    Gazaliev, AM
    Fazylov, SD
    Aitpaeva, ZK
    Turdybekov, DM
    RUSSIAN JOURNAL OF ORGANIC CHEMISTRY, 2006, 42 (03) : 448 - 450
  • [4] Selective synthesis of imidazolidine-2-thiones via ring expansion of aziridine-2-carboxylates with isothiocyanates
    Tabarki, Mohamed Ali
    Besbes, Rafaa
    TETRAHEDRON LETTERS, 2016, 57 (34) : 3832 - 3836
  • [5] Design, synthesis, and cytotoxicity screening of new synthesized imidazolidine-2-thiones as VEGFR-2 enzyme inhibitors
    Zaki, Islam
    Ramadan, Heba M. M.
    El-Sayed, El-Sherbiny H.
    Abd El-Moneim, Mohamed
    ARCHIV DER PHARMAZIE, 2020, 353 (11)
  • [6] Synthesis, structures, and novel antimicrobial activity of silver(I) halide complexes of imidazolidine-2-thiones
    Aulakh, Jaspreet K.
    Lobana, Tarlok S.
    Sood, Henna
    Arora, Daljit S.
    Garcia-Santos, Isabel
    Kaur, Manpreet
    Jasinski, Jerry P.
    POLYHEDRON, 2020, 175 (175)
  • [7] SYNTHESIS OF 1-ARYL-(GLYCOFURANO)IMIDAZOLIDINE-2-THIONES FROM NEW 2-(ALKYLAMINO)-2-DEOXYHEXOSES
    PEREZ, JAG
    ALBARRAN, JCP
    REQUEJO, JLJ
    GONZALEZ, MA
    FERNANDEZBOLANOS, JM
    CARBOHYDRATE RESEARCH, 1984, 129 (JUL) : 131 - 142
  • [8] ACYLATION OF GLYCOFURANO[2,1-D]IMIDAZOLIDINE-2-THIONES - A STRUCTURAL REVISION
    GONZALEZ, MA
    REQUEJO, JLJ
    ALBARRAN, JCP
    MONTERO, MDR
    PEREZ, JAG
    CARBOHYDRATE RESEARCH, 1987, 161 (01) : 49 - 64
  • [9] N,N'-DISUBSTITUTED IMIDAZOLIDINE-2-THIONES AS LIGANDS IN COBALT(II) COMPLEXES
    DEVILLANOVA, FA
    VERANI, G
    TRANSITION METAL CHEMISTRY, 1980, 5 (01) : 42 - 45
  • [10] Synthesis of functionalized imidazolidine-2-thiones via NHC/base-promoted aza-benzoin/aza-acetalization domino reactions
    Di Carmine, Graziano
    Ragno, Daniele
    De Risi, Carmela
    Bortolini, Olga
    Giovannini, Pier Paolo
    Fantin, Giancarlo
    Massi, Alessandro
    ORGANIC & BIOMOLECULAR CHEMISTRY, 2017, 15 (41) : 8788 - 8801
12345