Reaction of 6-methyl-2-(2-oxo-2-phenyl-ethylidene)-2,3-dihydropyrimidin-4(1H)-one with hydrazine and hydroxylamine

被引：8

作者：

Yavolovskii, A. A. ^{[1
]}

Grishchuk, L. V. ^{[1
]}

Rakipov, I. M. ^{[1
]}

Stepanov, D. E. ^{[1
]}

Ivanov, Yu. E. ^{[1
]}

Kamalov, G. L. ^{[1
]}

机构：

[1] Natl Acad Sci Ukraine, AV Bogatsky Physicochem Inst, UA-65080 Odessa, Ukraine

来源：

CHEMISTRY OF HETEROCYCLIC COMPOUNDS | 2013年 / 48卷 / 10期

基金：

俄罗斯基础研究基金会;

关键词：

hydrazine; hydroxylamine; imidazole N-oxides; pyrazoles; pyrimidine oximes; pyrimidines; pyrimidine ring transformation;

D O I：

10.1007/s10593-013-1162-z

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The reaction of 6-methyl-2-(2-oxo-2-phenylethylidene)-2,3-dihydropyrimidin-4(1H)-one and of its nitrosation product with hydroxylamine stops at the stage of forming the corresponding oximes. The reaction of 6-methyl-2-(2-oxo-2-phenylethylidene)-2,3-dihydropyrimidin-4(1H)-one with hydrazine yields a mixture of 3-amino-5-phenylpyrazole and 3-methyl-2-pyrazolin-5-one in 71 and 62% yields, respectively. The ketoxime is used in the synthesis of a series of imidazole N(3)-oxides substituted at the 1, 4, and 5 positions of the imidazole ring.

引用

页码：1487 / 1491

页数：5

共 50 条

[21] Synthesis, anti-inflammatory, antiplatelet and in silico evaluations of (E)-3-(3-(2,3-dihydro-3-methyl-2-oxo-3H-benzoxazole-6-yl)-1-phenyl-1H-pyrazole-4-yl)acrylamides
Baytas, Sultan
Dural, Nilufer Nermin Turan
Ozkan, Yesim
Simsek, Hasan Bolkan
Gursel, Turkiz
Unlu, Serdar
TURKISH JOURNAL OF CHEMISTRY, 2012, 36 (03) : 367 - 382
[22] Synthesis of 5-phenyl-2(1H)-pyrimidinone nucleosides
Krecmerova, M
Hrebabecky, H
Masojidkova, M
Holy, A
COLLECTION OF CZECHOSLOVAK CHEMICAL COMMUNICATIONS, 1996, 61 (03) : 458 - 477
[23] Reaction between acid N'-(2-oxo-2-phenyl-ethyl)hydrazides, acetylenic esters and alkyl isocyanides in the presence of silica sulfuric acid: One-pot synthesis of highly functionalized 2,3-dihydro-1H-pyrazoles
Ardakani, Leili Shaker
Mosslemin, Mohammad H.
Hassanabadi, Alireza
Hashemian, Saeedeh
PHOSPHORUS SULFUR AND SILICON AND THE RELATED ELEMENTS, 2021, 196 (11) : 1004 - 1009
[24] Facile conversion of Biginelli 3,4-dihydropyrimidin-2(1H)-thiones to 2-(2-hydroxy-2-arylvinyl) dihydropyrimidines via Eschenmoser coupling
Singh, Sukhdeep
Schober, Andreas
Gebinoga, Michael
Gross, G. Alexander
TETRAHEDRON LETTERS, 2009, 50 (16) : 1838 - 1843
[25] Voltammetric determination of hydroxylamine based on a catalytic reaction in the presence of 2,2,6,6-tetramethyl-4-acetylpiperidine-1-oxy radical
Tong, J
Dang, XJ
Li, HL
Yang, M
ANALYTICAL LETTERS, 1997, 30 (03) : 585 - 597
[26] Reaction of 4-aryl-2-hydroxy-4-oxo-2-butenoic acid N-(4-acetylaminosulfonylphenyl)amides with hydrazine hydrate and phenylhydrazine
V. L. Gein
O. V. Bobrovskaya
G. V. Seliverstov
P. A. Slepukhin
Russian Journal of General Chemistry, 2016, 86 : 300 - 304
[27] Reaction of 4-aryl-2-hydroxy-4-oxo-2-butenoic acid N-(4-acetylaminosulfonylphenyl)amides with hydrazine hydrate and phenylhydrazine
Gein, V. L.
Bobrovskaya, O. V.
Seliverstov, G. V.
Slepukhin, P. A.
RUSSIAN JOURNAL OF GENERAL CHEMISTRY, 2016, 86 (02) : 300 - 304
[28] Utility of 2-(5-methyl-1-phenyl-1H-pyrazol-4-yl)-2-oxo-N-phenylaceto-hydrazonoyl bromide as precursor for synthesis of new functionalized heterocycles
Abdelhamid, Abdou O.
Gomha, Sobhi M.
Abdelriheem, Nadia A.
SYNTHETIC COMMUNICATIONS, 2017, 47 (10) : 999 - 1005
[29] 5-cinnamoyl- and 5-(ethoxycarbonyl)-6-styryl derivatives of 4-aryl-3,4-dihydropyrimidin-2(1H)-ones
Kolosov, Maksim A.
Orlov, Valeriy D.
Vashchenko, Valeriy V.
Shishkina, Svetlana V.
Shishkinb, Oleg V.
COLLECTION OF CZECHOSLOVAK CHEMICAL COMMUNICATIONS, 2007, 72 (09) : 1219 - 1228
[30] Synthesis of new 2-substituted pyrido[2,3-d]pyrimidin-4(1H)-ones and their antibacterial activity
Narayana, B. Lakshmi
Rao, A. Raghu Ram
Rao, P. Shanthan
EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, 2009, 44 (03) : 1369 - 1376

← 1 2 3 4 5 →