Synthesis of 1,2,4-Thiadiazoles by Oxidative Dimerization of Carbothioamides by Using Oxone

被引:27
|
作者
Yoshimura, Akira [1 ]
Todora, Anthony D. [1 ]
Kastern, Brent J. [1 ]
Koski, Steven R. [1 ]
Zhdankin, Viktor V. [1 ]
机构
[1] Univ Minnesota, Dept Chem & Biochem, Duluth, MN 55812 USA
基金
美国国家科学基金会;
关键词
Oxidation; Oxone; Sulfur; Selenium; Heterocycles; C-H BONDS; HYPERVALENT IODINE; 3,5-DISUBSTITUTED 1,2,4-THIADIAZOLES; INTRAMOLECULAR OXIDATION; ALLOSTERIC MODULATOR; CONVENIENT; THIOAMIDES; CLEAVAGE; REARRANGEMENT; DERIVATIVES;
D O I
10.1002/ejoc.201402756
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
1,2,4-Thiadiazoles were efficiently synthesized in good yields through the oxidative dimerization of carbothioamides by using Oxone as a readily available, inexpensive, and environmentally safe oxidant. A similar reaction of phenylselenoamide led to the corresponding 1,2,4-phenylselenadiazole in high yield.
引用
收藏
页码:5149 / 5152
页数:4
相关论文
共 50 条
  • [41] Original ring contraction of triazine derivatives to 1,2,4-thiadiazoles
    Kikelj, Vincent
    Julienne, Karine
    Meslin, Jean-Claude
    Deniaud, David
    TETRAHEDRON LETTERS, 2009, 50 (42) : 5802 - 5804
  • [42] Synthesis and Antitumor Properties of New 1,2,4-Triazoles and 1,3,4-Thiadiazoles
    T. R. Ovsepyan
    F. G. Arsenyan
    L. E. Nersesyan
    I. S. Danielyan
    A. G. Agaronyan
    R. G. Melik-Ogandzhanyan
    Pharmaceutical Chemistry Journal, 2017, 50 : 724 - 727
  • [43] MASS SPECTRA .1. MASS SPECTRA OF 1,2,4-THIADIAZOLES
    MILLER, AH
    PANCIROV, RJ
    JOURNAL OF HETEROCYCLIC CHEMISTRY, 1971, 8 (01) : 163 - &
  • [44] NEW SYNTHESIS OF 3-AMINO-5-ALKYL-1,2,4-THIADIAZOLES
    JUNGE, B
    ANNALEN DER CHEMIE-JUSTUS LIEBIG, 1975, (11): : 1961 - 1966
  • [45] 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
  • [46] STRUCTURE OF 5-AMINO-1,2,4-THIADIAZOLES
    SHOEB, A
    POPLI, SP
    INDIAN JOURNAL OF CHEMISTRY, 1963, 1 (01): : 55 - &
  • [47] Green Chemistry in Organic Synthesis: Recent Update on Green Catalytic Approaches in Synthesis of 1,2,4-Thiadiazoles
    Rubab, Laila
    Anum, Ayesha
    Al-Hussain, Sami A.
    Irfan, Ali
    Ahmad, Sajjad
    Ullah, Sami
    Al-Mutairi, Aamal A.
    Zaki, Magdi E. A.
    CATALYSTS, 2022, 12 (11)
  • [48] THIADIAZOLES .16. 5-SUBSTITUTED 3-NITROAMINO- 1,2,4-THIADIAZOLES
    GODFREY, LEA
    KURZER, F
    JOURNAL OF THE CHEMICAL SOCIETY, 1963, (SEP): : 4566 - &
  • [49] SYNTHESIS OF 2-AMINO-1-3,4-THIADIAZOLES
    Khan, F. Nawaz
    Kumar, A. Sudheer
    Nithya, P.
    Roopan, S. Mohana
    INDIAN JOURNAL OF HETEROCYCLIC CHEMISTRY, 2009, 19 (01) : 83 - 84
  • [50] SYNTHESIS OF ORGANO-SILICON DERIVATIVES OF 1,2,4-TRIAZOLES AND 1,3,4-THIADIAZOLES
    GOLDIN, GS
    PODDUBNYI, VG
    KIRYANOVA, AN
    ZHURNAL OBSHCHEI KHIMII, 1980, 50 (04): : 860 - 863