An efficient synthesis of substituted 4,5-dihydroxyimidazolidin-2-ones by oxidation of imidazolin-2-ones with HNO3

被引:1
|
作者
V. Baranov, Vladimir [1 ]
Prakhov, Pavel D. [1 ,2 ]
Kolotyrkina, Natalya G. [1 ]
Kravchenko, Angelina N. [1 ]
机构
[1] Russian Acad Sci, ND Zelinsky Inst Organ Chem, Moscow 119991, Russia
[2] DI Mendeleev Univ Chem Technol Russia, Moscow 125047, Russia
关键词
4,5-dihydroxyimidazolidin-2-ones; nitric acid; oxidation; 4-imidazolin-2-ones; diastereomers; acyloins; ureas; CONDENSATION; GLYCOLURIL; UREAS; HYDANTOINS; BAMBUSURIL; CHEMISTRY; WATER; ACID;
D O I
10.1016/j.mencom.2024.01.035
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Previously unavailable 1,3-dialkyl-4,5-diaryl-4,5-dihydroxyimidazolidin-2-ones were obtained by the oxidation of 1,3-dialkyl-4,5-diaryl-4-imidazolin-2-ones with HNO3 (65 or 84% aq.). The scope of required 4-imidazolin-2-ones obtained from acyloins has been expanded, which provided preparation of new representatives of the title compounds.
引用
收藏
页码:116 / 118
页数:3
相关论文
共 50 条
  • [21] RING CONTRACTION OF 1,2,4-TRIAZIN-3-ONES TO IMIDAZOLIN-2-ONES AND 1,2,3-TRIAZOLES
    REES, CW
    SALE, AA
    JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1973, (06): : 545 - 550
  • [22] One-pot facile synthesis of 1,3,4-trisubstituted imidazolin-2-ones
    Cheng, YF
    Hu, YZ
    JOURNAL OF CHEMICAL RESEARCH, 2004, (04) : 292 - 293
  • [23] ACTION OF HYDROGEN-PEROXIDE ON SOME 2-AMINOOXAZOLES AND IMIDAZOLIN-2-ONES - ISOLATION OF HYDROPEROXYIMIDAZOLIDIN-2-ONES
    GINANNESCHI, M
    CHELLI, M
    RAPI, G
    JOURNAL OF HETEROCYCLIC CHEMISTRY, 1985, 22 (06) : 1675 - 1678
  • [24] FORMATION OF 1-(2-HYDROXYPHENYL)-4-SUBSTITUTED 4-IMIDAZOLIN-2-ONES AND 4,5-SUBSTITUTED 4-IMIDAZOLIN-2-ONES IN THE REACTION OF 3-[2-(HYDROXYIMINO)ALKYL]-2-BENZOXAZOLONES WITH SODIUM DITHIONITE
    LOZANOVA, C
    KALCHEVA, V
    SIMOV, D
    JOURNAL FUR PRAKTISCHE CHEMIE, 1989, 331 (06): : 1007 - 1010
  • [25] Synthesis of (S)-N-hydantoinoalkylglycoluriles by one-pot double cyclisation of chiral α,ω-diureido acids under the action of 4,5-dihydroxyimidazolidin-2-ones
    Chikunov, IE
    Kravchenko, AN
    Belyakov, PA
    Lebedev, OV
    Makhova, NN
    MENDELEEV COMMUNICATIONS, 2005, 15 (02) : 67 - 69
  • [26] An efficient synthesis of 2-alkylthio5-phenylmethylidene-4H-imidazolin-4-ones
    Ding, MW
    Sun, Y
    Liu, ZJ
    SYNTHETIC COMMUNICATIONS, 2003, 33 (08) : 1267 - 1274
  • [27] FORMATION OF SUBSTITUTED PTERIDINES FROM 5,6-DIAMINOPYRIMIDINES AND N-(ARYLSULFONYL)IMIDAZOLIN-2-ONES
    ZAVYALOV, SI
    ZAVOZIN, AG
    BULLETIN OF THE ACADEMY OF SCIENCES OF THE USSR DIVISION OF CHEMICAL SCIENCE, 1981, 30 (07): : 1355 - 1357
  • [28] An easy one-step synthesis of imidazolin-2-ones from phthalic anhydrides and their antioxidant evaluation
    Lopez, Hector S.
    Enciso, Jose E.
    Ochoa-Teran, Adrian
    Velazquez, Juan I.
    Sarmiento, Juan I.
    MENDELEEV COMMUNICATIONS, 2016, 26 (01) : 69 - 71
  • [29] SYNTHESIS OF 4,5-BIFUNCTIONALLY SUBSTITUTED IMIDAZOLIDIN-2-ONES
    SHUTALEV, AD
    KHIMIYA GETEROTSIKLICHESKIKH SOEDINENII, 1993, (12): : 1645 - 1649
  • [30] Heteroannulation Reaction of α-Aminoketones for the Efficient Synthesis of 4-Imidazolin-2-ones and 2-Thiones
    Rebollar, Araceli
    Bautista, Rafael
    Gutierrez, Rsuini U.
    Espinoza-Hicks, Carlos
    Mendieta, Aaron
    Zarate-Zarate, Daniel
    Martinez-Mora, Eder I.
    Labarrios-Moran, Ehecatl M.
    Vazquez, Miguel A.
    Delgado, Francisco
    Tamariz, Joaquin
    JOURNAL OF THE BRAZILIAN CHEMICAL SOCIETY, 2022, 33 (01) : 13 - +