Some properties of 1-hydroxy-1H-imidazole-2-carboxylic acid esters

被引：1
|
作者：
Nikolaenkova, Elena B. [1 ]
Grishchenko, Stanislav Yu. [1 ]
Krasnov, Vyacheslav I. [1 ]
Tikhonov, Alexsei Ya. [1 ]
机构：
[1] Russian Acad Sci, N N Vorozhtsov Novosibirsk Inst Organ Chem, Siberian Branch, 9 Akademika Lavrentieva Ave, Novosibirsk 630090, Russia
来源：
CHEMISTRY OF HETEROCYCLIC COMPOUNDS | 2024年 / 60卷 / 9-10期
关键词：
amides; esters of 1-hydroxy-1H-imidazole-2-carboxylic acids; hydrazides; alkylation; bromination; nitration; reduction;
D O I：
10.1007/s10593-024-03371-7
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
The corresponding amides and hydrazides were obtained by the reaction of 1-hydroxy-1H-imidazole-2-carboxylates with amines and hydrazine. In the reaction of an ester of 1-methoxy-4-methyl-5-(thiophen-2-yl)-1H-imidazole-2-carboxylic acid with NBS, bromination occurred at the thiophene ring, whereas in the reaction with 1,3-dibromo-5,5-dimethylhydantoin it took place at both the methyl group and the thiophene ring; its nitration led to mononitro- or dinitrothiophene derivatives. The reaction of 1-hydroxy-1H-imidazole-2-carboxylates with chloroacetone in Me2CO in the presence of Et3N resulted in the formation of reduced compounds.
引用
收藏
页码：529 / 535
页数：7
相关论文
共 50 条
  • [1] STEROIDAL IMIDAZOLE-1-CARBOXYLIC ACID-ESTERS
    FAHRENHO.KE
    BORIS, A
    KENNEDY, TW
    KIERSTEA.RW
    JOURNAL OF MEDICINAL CHEMISTRY, 1974, 17 (03) : 337 - 342
  • [2] 1-Methyl-4-nitro-1H-imidazole-2-carboxylic acid dihydrate
    Wu, HQ
    Liu, ZG
    Ng, SW
    ACTA CRYSTALLOGRAPHICA SECTION E-CRYSTALLOGRAPHIC COMMUNICATIONS, 2005, 61 : O3759 - O3760
  • [3] 1-(Dicyanomethylene)-3-hydroxy-1H-indene-2-carboxylic Acid
    Usova, Sofia D.
    Knyazeva, Ekaterina A.
    Rakitin, Oleg A.
    MOLBANK, 2024, 2024 (03)
  • [4] α-(1H-imidazol-1-yl)alkyl (IMIDA) carboxylic acid esters as prodrugs of carboxylic acid containing drugs
    Majumdar, Susruta
    Spaeth, Maren Mueller
    Sivendran, Sashikala
    Juntunen, Juha
    Thomas, Joshua D.
    Sloan, K. B.
    TETRAHEDRON LETTERS, 2007, 48 (26) : 4609 - 4611
  • [5] Synthesis and Structure of 5-(2-Alkoxy-2-oxoethyl)-1,2-diaryl-4-hydroxy-1H-pyrrole-3-carboxylic Acid Esters
    Mukovoz, P. P.
    Slepukhin, P. A.
    El'tsov, O. S.
    Ganebnykh, I. N.
    Gorbunova, A. V.
    Peshkov, S. A.
    RUSSIAN JOURNAL OF ORGANIC CHEMISTRY, 2018, 54 (04) : 554 - 563
  • [6] Synthesis and Structure of 5-(2-Alkoxy-2-oxoethyl)-1,2-diaryl-4-hydroxy-1H-pyrrole-3-carboxylic Acid Esters
    P. P. Mukovoz
    P. A. Slepukhin
    O. S. El’tsov
    I. N. Ganebnykh
    A. V. Gorbunova
    S. A. Peshkov
    Russian Journal of Organic Chemistry, 2018, 54 : 554 - 563
  • [7] Preparation of 2-unsubstituted 5-aryl(hetaryl)-1-hydroxy-1H-imidazoles from of 4-aryl(hetaryl)-1-hydroxy-2,5-dihydro-1H-imidazole-2-carboxylic acid 3-oxides
    Elena B. Nikolaenkova
    Stanislav Yu. Grishchenko
    Tatyana V. Rybalova
    Alexei Ya. Tikhonov
    Chemistry of Heterocyclic Compounds, 2023, 59 : 752 - 757
  • [8] Preparation of 2-unsubstituted 5-aryl(hetaryl)-1-hydroxy-1H-imidazoles from of 4-aryl(hetaryl)-1-hydroxy-2,5-dihydro-1H-imidazole-2-carboxylic acid 3-oxides
    Nikolaenkova, Elena B.
    Grishchenko, Stanislav Yu.
    Rybalova, Tatyana V.
    Tikhonov, Alexei Ya.
    CHEMISTRY OF HETEROCYCLIC COMPOUNDS, 2023, 59 (11-12) : 752 - 757
  • [9] POLYMERIC IMIDAZOLE CARBOXYLIC-ACIDS .1. SYNTHESIS AND PROPERTIES OF SOME CROSS-LINKED POLY(VINYLIMIDAZOLE CARBOXYLIC ACID)S
    MANECKE, G
    SCHLEGEL, R
    MAKROMOLEKULARE CHEMIE-MACROMOLECULAR CHEMISTRY AND PHYSICS, 1976, 177 (11): : 3191 - 3205
  • [10] INTERACTION OF NITROMETHANE WITH ESTERS AND AMIDES OF 2-OXO-2H-1-BENZOPYRANE-3-CARBOXYLIC ACID
    BOJILOVA, A
    KOSTADINOVA, T
    IVANOV, C
    SYNTHETIC COMMUNICATIONS, 1989, 19 (17) : 2963 - 2975
12345