Synthesis of 5-alkyl(aryl)-2-alkylsulfanyl(alkoxy)-4-hydroxy-6H-1,3-oxazin-6-ones

被引：4
|
作者：
Lalaev, BY [1 ]
Yakovlev, IP [1 ]
Zakhs, VE [1 ]
机构：
[1] St Petersburg State Chem & Pharmaceut Acad, St Petersburg, Russia
来源：
RUSSIAN JOURNAL OF GENERAL CHEMISTRY | 2005年 / 75卷 / 03期
关键词：
Ether; Benzene; Toluene; Boiling; Diethyl;
D O I：
10.1007/s11176-005-0245-7
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
Alkyl carbarnates and S-alkyl thiocarbamates react with substituted malonyl dichlorides in boiling benzene to give the corresponding 2,5-substituted 4-hydroxy-6H-1,3-oxazin-6-ones. The reaction of S-methyl thiocarbamate with unsubstituted malonyl dichloride in boiling diethyl ether or benzene leads to formation of S-methyl (3-methylsulfanylaminocarbonyl-3-oxopropionyl)thiocarbamate and is not accompanied by cyclization, whereas in boiling toluene 4-hydroxy-2-methylsulfanyl-6H-1,3-oxazin-6-one is obtained.
引用
收藏
页码：432 / 436
页数：5
相关论文
共 50 条
  • [1] Synthesis of 5-Alkyl(aryl)-2-alkylsulfanyl(alkoxy)-4-hydroxy-6H-1,3-oxazin-6-ones
    B. Yu. Lalaev
    I. P. Yakovlev
    V. E. Zakhs
    Russian Journal of General Chemistry, 2005, 75 : 432 - 436
  • [2] Reactions of 2-alkylsulfanyl- and 2-alkoxy-4-hydroxy-6H-1,3-oxazin-6-ones with O-nucleophiles
    Lalaev, B. Yu
    Yakovlev, I. P.
    Kuz'mich, N. N.
    Ksenofontova, G. V.
    Zakhs, V. E.
    RUSSIAN JOURNAL OF GENERAL CHEMISTRY, 2010, 80 (10) : 2043 - 2047
  • [3] Reactions of 2-alkylsulfanyl- and 2-alkoxy-4-hydroxy-6H-1,3-oxazin-6-ones with O-nucleophiles
    B. Yu. Lalaev
    I. P. Yakovlev
    N. N. Kuz’mich
    G. V. Ksenofontova
    V. E. Zakhs
    Russian Journal of General Chemistry, 2010, 80 : 2043 - 2047
  • [4] NOVEL SYNTHESIS OF ACYLAMINOMETHYLENE MELDRUMS ACIDS AND THEIR THERMOLYSIS TO 4-METHYLTHIO-2-ARYL-6H-1,3-OXAZIN-6-ONES AND 4-AMINO-2-ARYL-6H-1,3-OXAZIN-6-ONES
    HUANG, X
    CHEN, BC
    WU, GY
    CHEN, HB
    SYNTHETIC COMMUNICATIONS, 1991, 21 (10-11) : 1213 - 1221
  • [5] Reaction of 2,5-substituted 4-hydroxy-6H-1,3-oxazin-6-ones with benzimidazol-2-ylhydrazine
    Ovsyannikova, L. N.
    Lalaev, B. Yu.
    Yakovlev, I. P.
    Semakova, T. L.
    RUSSIAN JOURNAL OF ORGANIC CHEMISTRY, 2016, 52 (04) : 605 - 606
  • [6] Reaction of 2,5-substituted 4-hydroxy-6H-1,3-oxazin-6-ones with benzimidazol-2-ylhydrazine
    L. N. Ovsyannikova
    B. Yu. Lalaev
    I. P. Yakovlev
    T. L. Semakova
    Russian Journal of Organic Chemistry, 2016, 52 : 605 - 606
  • [7] Reaction of 4-hydroxy-6H-1,3-oxazin-6-ones with guanidine. Synthesis of new 1,3,5-triazine derivatives
    Chernov, N. M.
    Yakovlev, I. P.
    Zakhs, V. E.
    Semakova, T. L.
    Ksenofontova, G. V.
    RUSSIAN JOURNAL OF GENERAL CHEMISTRY, 2015, 85 (11) : 2578 - 2582
  • [8] Reaction of 4-hydroxy-6H-1,3-oxazin-6-ones with guanidine. Synthesis of new 1,3,5-triazine derivatives
    N. M. Chernov
    I. P. Yakovlev
    V. E. Zakhs
    T. L. Semakova
    G. V. Ksenofontova
    Russian Journal of General Chemistry, 2015, 85 : 2578 - 2582
  • [9] The reaction of 4-hydroxy-6H-1,3-oxazin-6-ones with amidines - a route to access new 1,3,5-triazine derivatives
    Levshukova, Polina O.
    Kolesnik, Denis A.
    Dosina, Margarita O.
    Yakovlev, Igor P.
    Tunguskova, Lidiya A.
    Kuvaeva, Elena V.
    Semakova, Tamara L.
    Ksenofontova, Galina V.
    Pokhodnya, Yurii G.
    CHEMISTRY OF HETEROCYCLIC COMPOUNDS, 2024, 60 (1-2) : 48 - 51
  • [10] Reactions of 4-Hydroxy-5-methyl(phenyl)-2-styryl-6H-1,3-oxazin-6-ones with Nucleophiles
    A. V. Komarov
    I. P. Yakovlev
    D. V. Novikov
    V. E. Zakhs
    Russian Journal of General Chemistry, 2003, 73 : 1936 - 1941
12345