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
  • [21] An efficient synthesis of novel coumarinyldihydropyrimidin-2-thiones via coumarinylenones
    Tyagi, Abhilash
    Mahiya, Kuldeep
    Kumar, Rajesh
    Singh, Sukhdev
    SYNTHETIC COMMUNICATIONS, 2024, 54 (01) : 41 - 49
  • [22] Synthesis, structures and antimicrobial activity of copper derivatives of N-substituted imidazolidine-2-thiones: unusual bio-activity against Staphylococcus epidermidis and Enterococcus faecalis
    Lobana, Tarlok S.
    Aulakh, Jaspreet K.
    Sood, Heena
    Arora, Daljit S.
    Garcia-Santos, Isabel
    Kaur, Manpreet
    Duff, Courtney E.
    Jasinski, Jerry P.
    NEW JOURNAL OF CHEMISTRY, 2018, 42 (12) : 9886 - 9900
  • [23] Metal derivatives of N-substituted imidazolidine-2-thiones with d10 metal ions (Zn-Hg): Synthesis, spectroscopy, ESI-mass and structures
    Lobana, Tarlok S.
    Sandhu, Amanpreet K.
    Jassal, Amanpreet K.
    Hundal, Geeta
    Mahajan, R. K.
    Jasinski, Jerry P.
    Butcher, Ray J.
    POLYHEDRON, 2015, 87 : 17 - 27
  • [24] SYNTHESIS OF NEW C-NUCLEOSIDE ANALOGS OF THE IMIDAZOLE FROM 1-ARYL-(1,2-DIDEOXY-BETA-D-GLYCERO-L-GLUCO-HEPTOFURANO)[2,1-D]-IMIDAZOLIDINE-2-THIONES
    PEREZ, JAG
    BRAVO, PA
    VICENTE, FR
    GARCIAHIERRO, JIF
    MOTA, JF
    CARBOHYDRATE RESEARCH, 1988, 176 (01) : 97 - 106
  • [25] Facile, efficient synthesis of polysubstituted thiazoles via α-nitroepoxides and thioureas
    Zhao, Donghong
    Guo, Shanshan
    Guo, Xiao
    Zhang, Guolin
    Yu, Yongping
    TETRAHEDRON, 2016, 72 (35) : 5285 - 5289
  • [26] Variable coordination and C-S bond cleavage activity of N-substituted imidazolidine-2-thiones towards copper: synthesis, spectroscopy, structures, ESI-mass and antimicrobial studies
    Aulakh, Jaspreet K.
    Lobana, Tarlok S.
    Sood, Henna
    Arora, Daljit S.
    Garcia-Santos, Isabel
    Hundal, Geeta
    Kaur, Manpreet
    Smolenski, Victoria A.
    Jasinski, Jerry P.
    DALTON TRANSACTIONS, 2017, 46 (04) : 1324 - 1339
  • [27] Efficient and Expeditious Synthesis of Di- and Trisubstituted Thiazoles in PEG Under Catalyst-Free Conditions
    Zhu, Dongjian
    Chen, Jiuxi
    Xiao, Huilong
    Liu, Miaochang
    Ding, Jinchang
    Wu, Huayue
    SYNTHETIC COMMUNICATIONS, 2009, 39 (16) : 2895 - 2906
  • [28] THIOGLUCIMIDAZOLES .12. 1-ARYL-4,5-(1,2-CIS-D-GLYCERO-L-GLUCO-HEPTOFURAN)IMIDAZOLIDINE-2-THIONES
    GARCIAGONZALEZ, F
    GALBISPEREZ, JA
    FERNANDEZGARCIAHIERRO, JI
    FERNANDEZBOLANOS, J
    ANALES DE QUIMICA, 1979, 75 (12): : 1002 - 1004
  • [29] Traceless solid-phase synthesis of 2,4,5-trisubstituted thiazoles
    Lee, IY
    Lee, JY
    Lee, HJ
    Gong, YD
    SYNLETT, 2005, (16) : 2483 - 2485
  • [30] New and efficient synthesis of bi- and trisubstituted indazoles
    Bouissane, L
    El Kazzouli, S
    Léger, JM
    Jarry, C
    Rakib, E
    Khouili, M
    Guillaumet, G
    TETRAHEDRON, 2005, 61 (34) : 8218 - 8225
12345