High yielding protocol for oxidative dimerization of primary thioamides: a strategy toward 3,5-disubstituted 1,2,4-thiadiazoles

被引:26
|
作者
Vanajatha, G. [1 ]
Reddy, V. Prabhakar [1 ]
机构
[1] Osmania Univ, Dept Chem, Hyderabad 500007, TS, India
关键词
Primary thioamides; Ceric ammonium nitrate; Oxidative dimerization; Symmetrically; Thiadiazoles; CERIUM(IV) AMMONIUM-NITRATE; MEDICINAL CHEMISTRY; DIARYL SELENOXIDE; ORGANIC-SYNTHESIS; MILD-STEEL; INHIBITORS; TRIBROMIDE; CONVERSION; MEDIA;
D O I
10.1016/j.tetlet.2016.04.029
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Ceric ammonium nitrate (CAN), a highly versatile reagent, was found to efficiently mediate the oxidative dimerization of primary thioamides in acetonitrile at room temperature leading to the rapid and expeditious synthesis of symmetrically 3,5-disubstituted 1,2,4-thiadiazoles in high yields. (C) 2016 Elsevier Ltd. All rights reserved.
引用
收藏
页码:2356 / 2359
页数:4
相关论文
共 50 条
  • [1] CONVENIENT PREPARATIONS OF 3,5-DISUBSTITUTED 1,2,4-THIADIAZOLES BY OXIDATIVE DIMERIZATION OF THIOAMIDES
    TAKIKAWA, Y
    SHIMADA, K
    SATO, K
    SATO, S
    TAKIZAWA, S
    BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN, 1985, 58 (03) : 995 - 999
  • [2] HIGHLY EFFICIENT OXIDATIVE DIMERIZATION OF THIOAMIDES TO 3,5-DISUBSTITUTED 1,2,4-THIADIAZOLES MEDIATED BY DDQ
    Cheng, Dongping
    Luo, Ruiwen
    Zheng, Wen
    Yan, Jizhong
    SYNTHETIC COMMUNICATIONS, 2012, 42 (13) : 2007 - 2013
  • [3] A Simple and Convenient Method for the Synthesis of 3,5-disubstituted 1,2,4-thiadiazoles via Oxidative Dimerization of Primary Thioamides
    Bose, D. Subhas
    Reddy, K. Raghavender
    JOURNAL OF HETEROCYCLIC CHEMISTRY, 2017, 54 (01) : 769 - 774
  • [4] IBX/TEAB-mediated oxidative dimerization of thioamides: synthesis of 3,5-disubstituted 1,2,4-thiadiazoles
    Patil, Pravin C.
    Bhalerao, Dinesh S.
    Dangate, Prasad S.
    Akamanchi, Krishnacharya G.
    TETRAHEDRON LETTERS, 2009, 50 (42) : 5820 - 5822
  • [5] Facile access to 3,5-symmetrically disubstituted 1,2,4-thiadiazoles through phosphovanadomolybdic acid catalyzed aerobic oxidative dimerization of primary thioamides
    Yajima, Kazuhisa
    Yamaguchi, Kazuya
    Mizuno, Noritaka
    CHEMICAL COMMUNICATIONS, 2014, 50 (51) : 6748 - 6750
  • [6] ORGANIC HERBICIDES .6. 3,5-DISUBSTITUTED 1,2,4-THIADIAZOLES
    ZBIROVSKY, M
    STANEK, J
    MYSKA, J
    COLLECTION OF CZECHOSLOVAK CHEMICAL COMMUNICATIONS, 1971, 36 (12) : 4091 - +
  • [7] Hypervalent iodine in synthesis. 84. Facile synthesis of 3,5-disubstituted 1,2,4-thiadiazoles by oxidative dimerization of thioamides using polymer-supported iodobenzene diacetate
    Cheng, DP
    Chen, ZC
    SYNTHETIC COMMUNICATIONS, 2002, 32 (14) : 2155 - 2159
  • [8] Electrochemical Synthesis of 3,5-Disubstituted-1,2,4-thiadiazoles through NH4I-Mediated Dimerization of Thioamides
    Wang, Zi-Qiang
    Meng, Xiu-Jin
    Li, Qian-Yu
    Tang, Hai-Tao
    Wang, Heng-Shan
    Pan, Ying-Ming
    ADVANCED SYNTHESIS & CATALYSIS, 2018, 360 (21) : 4043 - 4048
  • [9] Screening of a series of 3,5-disubstituted 1,2,4-thiadiazoles for selectivity of cytotoxic action to cancer cells
    A. N. Proshin
    T. P. Trofimova
    O. N. Zefirova
    I. V. Zhirkina
    D. A. Skvortsov
    S. O. Bachurin
    Russian Chemical Bulletin, 2021, 70 : 510 - 514
  • [10] Screening of a series of 3,5-disubstituted 1,2,4-thiadiazoles for selectivity of cytotoxic action to cancer cells
    Proshin, A. N.
    Trofimova, T. P.
    Zefirova, O. N.
    Zhirkina, I., V
    Skvortsov, D. A.
    Bachurin, S. O.
    RUSSIAN CHEMICAL BULLETIN, 2021, 70 (03) : 510 - 514