Synthesis and intramolecular conversion of substituted 2-methyl-11-nitro-5,6-dihydro-2H-2,6-methanobenzo[g][1,3,5] oxadiazocin-4(3H)-ones in different solvents

被引：0
|
作者：
V. F. Sedova
V. P. Krivopalov
Yu. V. Gatilov
O. P. Shkurko
机构：
[1] Siberian Branch of the Russian Academy of Sciences,N. N. Vorozhtsov Novosibirsk Institute of Organic Chemistry
来源：
Russian Chemical Bulletin | 2014年 / 63卷
关键词：
salicylic aldehydes; Biginelli reaction; nitrodihydro-2,6-methanobenzo-[1,3,5]oxadiazocin-4(3; )-ones; intramolecular transformations;
D O I：
暂无
中图分类号：
学科分类号：
摘要：
A Biginelli reaction of 5-R-salicylic aldehydes (R = H, Me, Br) with nitroacetone and urea in each case leads to a predominant formation of 2R*,6S*,11S* diastereomers of 8-R-2-methyl-11-nitro-5,6-dihydro-2H-2,6-methanobenzo[g][1,3,5]oxadiazocin-4(3H)-one. In solutions in DMF and DMSO, these diastereomers undergo the oxadiazocine ring opening with setting a three-component equilibrium between predominant 4-(2-hydroxy-5-R-phenyl)-6-methyl5-nitro-3,4-dihydropyrimidin-2(1H)-ones and 2R*,6S*,11S* and 2R*,6S*,11R* diastereomers of methanobenzoxadiazocine as two minor components.
引用
收藏
页码：1378 / 1385
页数：7
相关论文
共 50 条
  • [1] Synthesis and intramolecular conversion of substituted 2-methyl-11-nitro-5,6-dihydro-2H-2,6-methanobenzo[g] [1,3,5] oxadiazocin-4(3H)-ones in different solvents
    Sedova, V. F.
    Krivopalov, V. P.
    Gatilov, Yu. V.
    Shkurko, O. P.
    RUSSIAN CHEMICAL BULLETIN, 2014, 63 (06) : 1378 - 1385
  • [2] Synthesis and intramolecular transformations of 8-substituted 11-nitro-2-phenyl-5,6-dihydro-2H-2,6-methanobenzo[g][1,3,5]oxadiazocin-4(3H)-one diastereomers
    Sedova, V. F.
    Krivopalov, V. P.
    Shkurko, O. P.
    RUSSIAN CHEMICAL BULLETIN, 2016, 65 (01) : 215 - 222
  • [3] Synthesis and intramolecular transformations of 8-substituted 11-nitro-2-phenyl-5,6-dihydro-2H-2,6-methanobenzo[g][1,3,5]oxadiazocin-4(3H)-one diastereomers
    V. F. Sedova
    V. P. Krivopalov
    O. P. Shkurko
    Russian Chemical Bulletin, 2016, 65 : 215 - 222
  • [4] 2-Methyl-11-nitro-5,6-dihydro-2H-2,6-methano-1,3,5-benzoxadiazocin-4(3H)-one: synthesis, crystal structure and tautomerism in dipolar aprotic solvents
    Sedova, Valentina F.
    Krivopalov, Viktor P.
    Gatilov, Yurii V.
    Shkurko, Oleg P.
    MENDELEEV COMMUNICATIONS, 2013, 23 (03) : 176 - 178
  • [5] Unexpected transformations of 11-acetyl-8-bromo-2-methyl-5,6-dihydro-2H-2,6-methano-1,3,5-benzoxadiazocin-4(3H)-one(thione)
    Valentina F. Sedova
    Viktor P. Krivopalov
    Oleg P. Shkurko
    Chemistry of Heterocyclic Compounds, 2017, 53 : 1163 - 1166
  • [6] Unexpected transformations of 11-acetyl-8-bromo-2-methyl-5,6-dihydro-2H-2,6-methano-1,3,5-benzoxadiazocin-4(3H)-one(thione)
    Sedova, Valentina F.
    Krivopalov, Viktor P.
    Shkurko, Oleg P.
    CHEMISTRY OF HETEROCYCLIC COMPOUNDS, 2017, 53 (10) : 1163 - 1166
  • [7] SATURATED HETEROCYCLES .46. SYNTHESIS OF 2-SUBSTITUTED-5,6-PENTAMETHYLENE-,5,6-HEXAMETHYLENEPYRIMIDIN-4(3H)-ONES AND 5,6-DECAMETHYLENEPYRIMIDIN-4(3H)-ONES
    BERNATH, G
    LAZAR, J
    GERA, L
    GONDOS, G
    ECSERY, Z
    ACTA CHIMICA HUNGARICA-MODELS IN CHEMISTRY, 1984, 115 (03): : 231 - 235
  • [8] Green chemistry approach to the synthesis of 3-substituted-quinazolin-4(3H)-ones and 2-methyl-3-substituted-quinazolin-4(3H)-ones and biological evaluation
    Komar, Mario
    Molnar, Maja
    Jukic, Marijana
    Glavas-Obrovac, Ljubica
    Opacak-Bernardi, Teuta
    GREEN CHEMISTRY LETTERS AND REVIEWS, 2020, 13 (02) : 93 - 101
  • [9] SYNTHESIS OF 2-SUBSTITUTED BENZO[G]QUINAZOLIN-4(3H)-ONES
    KUMAR, PR
    REDDY, MS
    INDIAN JOURNAL OF CHEMISTRY SECTION B-ORGANIC CHEMISTRY INCLUDING MEDICINAL CHEMISTRY, 1994, 33 (09): : 883 - 884
  • [10] Synthesis of Substituted 4-Amino-1,3,5-triaryl-1H-pyrrol-2(5H)-ones
    Aleksanyan, M. V.
    Harutyunyan, G. K.
    Gasparyan, S. P.
    RUSSIAN JOURNAL OF GENERAL CHEMISTRY, 2024, 94 (05) : 1031 - 1039
12345