Synthesis and Asymmetric Oxidation of (Caranylsulfanyl)-1H-imidazoles

被引：6
|
作者：
Demakova, Marina Y. [1 ]
Sudarikov, Denis V. [1 ]
Rubtsova, Svetlana A. [1 ]
Frolova, Larisa L. [1 ]
Popov, Alexey V. [1 ]
Slepukhin, Pavel A. [2 ]
Kuchin, Alexander V. [1 ]
机构：
[1] RAS, Inst Chem, Komi Sci Ctr, Ural Div, RU-167982 Syktyvkar, Russia
[2] RAS, Inst Organ Synth, Ural Div, RU-620041 Ekaterinburg, Russia
来源：
HELVETICA CHIMICA ACTA | 2012年 / 95卷 / 06期
基金：
俄罗斯基础研究基金会;
关键词：
1H-Imidazoles; (caranylsulfanyl)-; Asymmetric oxidation; X-Ray crystallography; ALCOHOLS; ALKYLATION; SULFOXIDES; ALDEHYDES; SULFIDES; THIOLS;
D O I：
10.1002/hlca.201100484
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
For the first time 2-(cis-caran-4-ylsulfanyl)-1H-imidazole, 1-methyl-2-(cis-caran-4-ylsulfanyl)-1H-imidazole, and 2-(cis-caran-4-ylsulfanyl)-1H-benzimidazole (carane=3,7,7-trimethylbicyclo[4.1.0]heptane) were synthesized, and the asymmetric oxidation of these compounds was also carried out. It was shown that oxidation by the Bolm system and the modified system of Sharpless lead to corresponding sulfoxides with de values of 91100%.
引用
收藏
页码：940 / 950
页数：11
相关论文
共 50 条
  • [31] Polyfunctional imidazoles: VIII. 1-Aryl-4-chloro-5-[R-sulfanyl(sulfonyl)methyl]-1H-imidazoles
    A. N. Grozav
    V. A. Chornous
    A. A. Palamar
    M. V. Vovk
    Russian Journal of Organic Chemistry, 2014, 50 : 1335 - 1340
  • [32] AN ALTERNATIVE SYNTHETIC APPROACH TOWARDS 2, 4, 5- TRISUBSTITUTED 1H-IMIDAZOLES
    Babu, K.
    Surendhar, V.
    HETEROCYCLIC LETTERS, 2014, 4 (02): : 235 - 238
  • [33] Novel structural analogs of glyphosate based on azoles. 1. Synthesis of 1H-imidazoles containing carboxyl and phosphoryl groups in the ring
    N. V. Pavlenko
    T. I. Oos
    Yu. L. Yagupolskii
    A. van Almsick
    L. Willms
    Chemistry of Heterocyclic Compounds, 2011, 47 : 36 - 44
  • [34] Synthesis, evaluation, in silico ADMET screening, HYDE scoring, and molecular docking studies of synthesized 1-trityl-substituted 1H-imidazoles
    Rasul, Hezha O.
    JOURNAL OF THE IRANIAN CHEMICAL SOCIETY, 2023, 20 (12) : 2905 - 2916
  • [35] Synthesis and Anti-Candida Potential of Certain Novel 1-[(3-Substituted-3-phenyl)propyl]-1H-imidazoles
    Aboul-Enein, Mohamed Nabil
    El-Azzouny, Aida Abd El-Sattar
    Attia, Mohamed Ibrahim
    Saleh, Ola Ahmed
    Kansoh, Amany Lotfy
    ARCHIV DER PHARMAZIE, 2011, 344 (12) : 794 - 801
  • [36] Synthesis, evaluation, in silico ADMET screening, HYDE scoring, and molecular docking studies of synthesized 1-trityl-substituted 1H-imidazoles
    Hezha O. Rasul
    Journal of the Iranian Chemical Society, 2023, 20 : 2905 - 2916
  • [37] Studies on isocyanides and related compounds. Synthesis of 1-aryl-2-(tosylamino)-1H-imidazoles, a novel class of imidazole derivatives
    Bossio, R
    Marcaccini, S
    Pepino, R
    JOURNAL OF ORGANIC CHEMISTRY, 1996, 61 (06): : 2202 - 2203
  • [38] Synthesis and biological evaluation of aryl 1,2,4-oxadiazole incorporated (2-(oxazol)-1H-imidazoles as anticancer agents
    Bairi, Suresh
    Alagarsamy, Veerachamy
    Rachamalla, Shyam Sunder
    Eppakayala, Laxminarayana
    RESULTS IN CHEMISTRY, 2022, 4
  • [39] Facile synthesis of fully substituted 1H-imidazoles from oxime esters via dual photoredox/copper catalyzed multicomponent reactions
    Cao, Shujun
    Ma, Chongchong
    Teng, Xinjie
    Chen, Rongshun
    Li, Yun
    Yuan, Weidong
    Zhu, Yingguang
    ORGANIC CHEMISTRY FRONTIERS, 2022, 9 (24) : 6817 - 6825
  • [40] SYNTHESIS OF IMINO-2H-IMIDAZOLES AND IMINO-1H-IMIDAZOLES
    BUCHEL, KH
    ERDMANN, H
    CHEMISCHE BERICHTE-RECUEIL, 1977, 110 (09): : 3226 - 3227
12345