Synthesis of 4-[Alkylsulfanyl(sulfonyl)methyl]isoxazoles and-1H-pyrazoles from 3-[(Alkylsulfanyl)methyl]- pentane-2,4-diones

被引：11

作者：

Baeva, L. A. ^{[1
]}

Nugumanov, R. M. ^{[1
]}

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

Lyapina, N. K. ^{[1
]}

机构：

[1] Russian Acad Sci, Ufa Inst Chem, Pr Oktyabrya 71, Ufa 450054, Bashkortostan, Russia

来源：

RUSSIAN JOURNAL OF ORGANIC CHEMISTRY | 2018年 / 54卷 / 03期

关键词：

IN-VITRO; NUCLEOPHILIC CHEMISTRY; INHIBITORS; DISCOVERY;

D O I：

10.1134/S1070428018030120

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

New 4-[(alkylsulfanyl)methyl]- and 4-[(alkanesulfonyl)methyl]isoxazoles and -1H-pyrazoles were synthesized by reactions of 3-[(alkylsulfanyl)methyl]- and 3-[(alkanesulfonyl)methyl]pentane-2,4-diones with hydroxylamine and hydrazine, phenylhydrazine, semicarbazide, or thiosemicarbazide, respectively. The heterocyclization of 3-[(alkylsulfanyl)methyl]pentane-2,4-diones with thiosemicarbazide and semicarbazide hydrochloride was accompanied by elimination of amide or thioamide group. 3-[(Alkanesulfonyl)methyl]pentane- 2,4-diones were found to exist in solution as enol tautomers; they were prepared by oxidation of the corresponding 3-[(alkylsulfanyl)methyl]pentane-2,4-diones with hydrogen peroxide in acetic acid in the presence of a catalytic amount of sulfuric acid.

引用

页码：444 / 451

页数：8

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