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
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
  • [31] NEW METHOD FOR SYNTHESIS OF HALOZINCALCOHOLATES - SYNTHESIS OF SUBSTITUTED 1,3-OXAZIN-6-ONES
    LAPKIN, II
    SEMENOV, VI
    BELONOVICH, MI
    ZHURNAL ORGANICHESKOI KHIMII, 1977, 13 (06): : 1328 - 1330
  • [32] Potentiometric study on acid properties of some 4-hydroxy-6H-1,3-oxazin-6-ones.: Structure-biological activity relationship
    Lalaev, B. Yu.
    Petina, O. A.
    Kuz'mich, N. N.
    Yakovlev, I. P.
    Alekseeva, G. M.
    Zakhs, V. E.
    RUSSIAN JOURNAL OF GENERAL CHEMISTRY, 2006, 76 (04) : 645 - 648
  • [33] RING-ENLARGEMENT OF ISOXAZOL-5-ONES TO 1,3-OXAZIN-6-ONES
    RISITANO, F
    GRASSI, G
    FOTI, F
    CARUSO, F
    LOVECCHIO, G
    JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1979, (06): : 1522 - 1524
  • [34] Potentiometric study on acid properties of some 4-hydroxy-6H-1,3-oxazin-6-ones. Structure-biological activity relationship
    B. Yu. Lalaev
    O. A. Petina
    N. N. Kuz’mich
    I. P. Yakovlev
    G. M. Alekseeva
    V. E. Zakhs
    Russian Journal of General Chemistry, 2006, 76 : 645 - 648
  • [35] THERMOLYSIS OF 1,3-OXAZIN-6-ONES TO 2,4,6-TRISUBSTITUTED PYRIDINES
    BUSCHMANN, E
    STEGLICH, W
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 1974, 13 (07) : 484 - 484
  • [36] Traceless Solid-Phase Synthesis of Heteroannulated 1,3-Oxazin-6-ones
    Che, Jun
    Raghavendra, Makam S.
    Lam, Yulin
    JOURNAL OF COMBINATORIAL CHEMISTRY, 2009, 11 (03): : 378 - 384
  • [37] Synthesis of 2-substituted 1,3-oxazin-6-ones by gas-phase pyrolysis
    McNab, H.
    Withell, K.
    Tetrahedron, 52 (09):
  • [38] Synthesis of 2-substituted 1,3-oxazin-6-ones by gas-phase pyrolysis
    McNab, H
    Withell, K
    TETRAHEDRON, 1996, 52 (09) : 3163 - 3170
  • [39] SYNTHESIS OF 6-ARYL-2-(2-BENZIMIDAZOLYLAMINO)-1,3-OXAZIN-4-ONES
    ANDREICHIKOV, YS
    NEKRASOV, DD
    ZHURNAL ORGANICHESKOI KHIMII, 1988, 24 (10): : 2237 - 2238
  • [40] Base-promoted [3+3] cyclization of cyclopropenones and cyclopropenethiones with amides for the synthesis of 6H-1,3-oxazin-6-ones and 6H-1,3-thiazin-6-ones
    Niu, Ben
    Jiang, Bo
    Yu, Liu-Zhu
    Shi, Min
    ORGANIC CHEMISTRY FRONTIERS, 2018, 5 (08): : 1267 - 1271