Transformations of 5-methyl-2-phenyl-2,4-dihydro-3H-pyrazol-3-one under various conditions of cyclopropyldiazonium generation

被引：2

作者：

Okonnishnikova, G. P. ^{[1
]}

Kostyuchenko, I. V. ^{[1
]}

Shulishov, E. V. ^{[1
]}

Tomilov, Yu. V. ^{[1
]}

机构：

[1] Russian Acad Sci, ND Zelinskii Organ Chem Inst, Moscow 119991, Russia

来源：

RUSSIAN CHEMICAL BULLETIN | 2006年 / 55卷 / 12期

关键词：

cyclopropyldiazonium; cyclopropylhydrazone; N-cyclopropylnitrone; spiro[isoxazolidine-3,4 '-pyrazoline; azo coupling; nitrosation; 1,3-dipolar addition;

D O I：

10.1007/s11172-006-0577-4

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Cyclopropyldiazonium generated by basic decomposition of N-cyclopropyl-N-nitrosourea easily entered into an azo coupling reaction with 5-methyl-2-phenyl-2,4-dihydro-3H-pyrazol-3-one (2) to give the corresponding cyclopropylhydrazone in up to 90% yield. Competitive processes occurring under the conditions of cyclopropyldiazonium generation by nitrosation of cyclopropylamine with butyl nitrite mainly include nitrosation of the starting pyrazolone 2. Subsequent transformations of the resulting heterocyclic 3-methyl-1-phenyl-1H-pyrazole-4,5-dione 4-oxime yield 4-[cyclopropyl(oxido)imino]-5-methyl-2-phenyl-2,4-dihydro-3H-pyrazol-3-one.

引用

页码：2233 / 2237

页数：5

共 50 条

[1] Transformations of 5-methyl-2-phenyl-2,4-dihydro-3H-pyrazol-3-one under various conditions of cyclopropyldiazonium generation
G. P. Okonnishnikova
I. V. Kostyuchenko
E. V. Shulishov
Yu. V. Tomilov
Russian Chemical Bulletin, 2006, 55 : 2233 - 2237
[2] Crystal structure of (Z)-4-(((4-fluorophenyl)amino)(furan-2-yl)methylene)-5-methyl-2-phenyl-2,4-dihydro-3H-pyrazol-3-one
Wu, Qiong
Zhang, Li
Gao, Jun-Jie
Yang, Liu
Zhang, Heng-Qiang
Fan, Li-Li
Zhang, Ya-Zhai
ZEITSCHRIFT FUR KRISTALLOGRAPHIE-NEW CRYSTAL STRUCTURES, 2022, 237 (04): : 647 - 649
[3] Synthesis, characterization and computational studies on (E)-4-(1-((2-hydroxyphenyl)imi no) hexyl)-5-methyl-2-phenyl-2,4-dihydro-3H-pyrazol-3-one
Ukwueze, Nkechinyere N.
Ezeorah, Chigozie J.
Onyeyilim, Ebuka L.
Uzoewulu, Chiamaka P.
Okoro, Uchechukwu C.
Ukoha, Pius O.
Nnaji, Nnaemeka
Anarado, Chigozie J. O.
Dege, Necmi
Obasi, Nnamdi L.
Ugwu, Albert O.
Onyeisi, Ngozi M.
Lobb, Kevin
Ujam, Qguejiofo T.
JOURNAL OF MOLECULAR STRUCTURE, 2025, 1323
[4] Reactivity of Peroxyl Radicals with 5-Methyl-4-[(Propylsulfanyl)methyl]-2,4-Dihydro-3H-Pyrazol-3-one
Yakypova, L. R.
Baeva, L. A.
Safiullin, R. L.
KINETICS AND CATALYSIS, 2021, 62 (01) : 56 - 61
[5] Reactivity of Peroxyl Radicals with 5-Methyl-4-[(Propylsulfanyl)methyl]-2,4-Dihydro-3H-Pyrazol-3-one
L. R. Yakypova
L. A. Baeva
R. L. Safiullin
Kinetics and Catalysis, 2021, 62 : 56 - 61
[6] EXTRACTION OF PROMETHIUM COMPLEX WITH 4-BENZOYL-5-METHYL-2-PHENYL-2,4-DIHYDRO-3H-PYRAZOL-3-ONE INTO FREON 113 AND ITS MIXTURES WITH BENZENES
LINHART, P
COLLECTION OF CZECHOSLOVAK CHEMICAL COMMUNICATIONS, 1991, 56 (10) : 2096 - 2099
[7] MASS-SPECTRAL FRAGMENTATION-PATTERN OF 5-METHYL-4-[(PHENYLAMINO)METHYLENE]-2,4-DIHYDRO-3H-PYRAZOL-3-ONE AND ITS 2-METHYL AND 2-PHENYL DERIVATIVES
KEATS, NG
ROCKLEY, JE
SUMMERS, LA
JOURNAL OF HETEROCYCLIC CHEMISTRY, 1982, 19 (01) : 55 - 59
[8] Action of primary aliphatic and aromatic amines on 2,4-dihydro-5-methyl-2-phenyl-4-benzylidene-3H-pyrazol-3-one
Youssef, ASA
Kandeel, KA
AFINIDAD, 2000, 57 (488) : 268 - 272
[9] SYNTHESES AND CHARACTERIZATION OF SOME METAL-COMPLEXES OF 2,4-DIHYDRO-5-METHYL-2-PHENYL-3H-PYRAZOL-3-ONE-THIOSEMICARBAZONE
SINGH, HB
MAHESHWARI, S
WASI, N
OM, H
SYNTHESIS AND REACTIVITY IN INORGANIC AND METAL-ORGANIC CHEMISTRY, 1985, 15 (03): : 335 - 352
[10] Synthesis and crystal structure of (Z)-4-((1-(3-fluorophenyl)-1H-1,2,3-triazol-4-yl)methylene)-5-methyl-2-phenyl-2,4-dihydro-3H-pyrazol-3-one, C19H14FN5O
Konovalova, Irina S.
Geleverya, Anna O.
Semenets, Anton
Kovalenko, Sergiy M.
Reiss, Guido J.
ZEITSCHRIFT FUR KRISTALLOGRAPHIE-NEW CRYSTAL STRUCTURES, 2024, 239 (05): : 877 - 880

← 1 2 3 4 5 →