Reaction of 5-arylfuran-2(3H)-ones with amines

被引:2
|
作者
Potikha, L. M. [1 ]
Lysakovskii, A. A. [1 ]
Kovtunenko, V. A. [1 ]
Turov, A. V. [1 ]
机构
[1] Taras Shevchenko Kiev Natl Univ, UA-01033 Kiev, Ukraine
关键词
ACID;
D O I
10.1134/S1070428009120112
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
5-(4-Chlorophenyl)- and 5-phenylfuran-2(3H)-ones reacted with guanidine carbonate at the methylene group in the unsaturated lactone molecule, leading to the formation of 4-(2-aryl-5-oxo-2,5-dihydrofuran-2-yl)-5-aryltetrahydrofuran-2-ones, while 5-(4-methylphenyl)furan-2(3H)-one under analogous conditions gave rise to N,N'-bis[4-(4-methylphenyl)-4-oxobutanoyl]guanidine. The reactions of 5-arylfuran-2(3H)- ones with thioacetamide afforded 4-aryl-N-{1-[5-aryl-2-oxo-2,3-dihydrofuran-3-ylidene]ethyl}-4-oxobutanamides. The corresponding N-(4-aryl-4-oxobutanoyl)thioureas were obtained by heating 5-arylfuran-2(3H)-ones with thiourea.
引用
收藏
页码:1818 / 1823
页数:6
相关论文
共 50 条
  • [41] Copper-catalyzed consecutive reaction to construct quinazolin-4(3H)-ones and pyrido[2,3-d]pyrimidin-4(3H)-ones
    Li, Ting
    Chen, Minglu
    Yang, Lei
    Xiang, Zhengxin
    Wang, Yongwei
    Li, Fei
    Chen, Dongyin
    TETRAHEDRON, 2016, 72 (06) : 868 - 874
  • [42] SYNTHESIS OF HETEROCYCLES .5. 1,3,4-THIADIAZOL-2(3H)-ONES
    KRISTINSSON, H
    WINKLER, T
    HELVETICA CHIMICA ACTA, 1982, 65 (08) : 2606 - 2621
  • [43] A novel synthesis of spiro[5H-1,4-diazepine-5,3′-[3H]indol]-2′(1′H)-ones and spiro[2H-1,5-benzodiazepine-2,3′-[3H]indol]-2′(1′H)-ones
    Bajpai, SN
    Jain, R
    Joshi, KC
    INDIAN JOURNAL OF CHEMISTRY SECTION B-ORGANIC CHEMISTRY INCLUDING MEDICINAL CHEMISTRY, 1997, 36 (11): : 1005 - 1008
  • [44] 5-ACYL-3-SUBSTITUTED-BENZOFURAN-2(3H)-ONES AS POTENTIAL ANTIINFLAMMATORY AGENTS
    CHAKRABARTI, JK
    EGGLETON, RJ
    GALLAGHER, PT
    HARVEY, J
    HICKS, TA
    KITCHEN, EA
    SMITH, CW
    JOURNAL OF MEDICINAL CHEMISTRY, 1987, 30 (09) : 1663 - 1668
  • [45] Isomerism and tautomerism of 5-fluoroalkyl-substituted 3-acetyldihydrofuran-2(3H)-ones
    M. I. Kodess
    E. G. Matochkina
    D. N. Bazhin
    T. I. Gorbunova
    A. Ya. Zapevalov
    Russian Journal of General Chemistry, 2009, 79 : 800 - 807
  • [46] Isomerism and tautomerism of 5-fluoroalkyl-substituted 3-acetyldihydrofuran-2(3H)-ones
    Kodess, M. I.
    Matochkina, E. G.
    Bazhin, D. N.
    Gorbunova, T. I.
    Zapevalov, A. Ya.
    RUSSIAN JOURNAL OF GENERAL CHEMISTRY, 2009, 79 (04) : 800 - 807
  • [47] PREPARATION OF 5-SUBSTITUTED-1,3,4-OXADIAZOL-2(3H)ONES AND THEIR REACTIONS
    STEMPEL, A
    ZELAUSKAS, J
    AESCHLIMANN, JA
    JOURNAL OF ORGANIC CHEMISTRY, 1955, 20 (04): : 412 - 418
  • [48] ACYLATED KETENIMINES AND ALLENES FROM OXAZOL-5(4H)-ONES AND FURAN-2(3H)-ONES
    BERSTERMANN, HM
    HARDER, R
    WINTER, HW
    WENTRUP, C
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1980, 19 (07): : 564 - 566
  • [49] ON THE MECHANISM OF FORMATION OF 1,3,4-THIADIAZOL-2(3H)-ONES IN THE REACTION OF HYDRAZONOYL HALIDES WITH 1,3,4-OXADIAZOLE-2(3H)-THIONES
    MOSSELHI, MAN
    ABDALLAH, MA
    ABBAS, IM
    MOHAMMED, SZ
    SHAWALI, AS
    JOURNAL OF CHEMICAL RESEARCH-S, 1995, (03): : 83 - 83
  • [50] A FACILE RETRO-ENE REACTION OF 5-(METHOXYAMINO)-3-ARYL-1,3,4-OXADIAZOL-2(3H)-ONES
    KLEIER, DA
    PILGRAM, KH
    JOURNAL OF HETEROCYCLIC CHEMISTRY, 1987, 24 (06) : 1643 - 1647