An unusual thionyl chloride-promoted C-C bond formation to obtain 4,4′-bipyrazolones

被引：7

作者：

Eller, Gernot A. ^{[1
]}

Vilkauskaite, Gyte ^{[1
,2
]}

Sackus, Algirdas ^{[2
,3
]}

Martynaitis, Vytas ^{[2
]}

Mamuye, Ashenafi Damtew ^{[1
]}

Pace, Vittorio ^{[1
]}

Holzer, Wolfgang ^{[1
]}

机构：

[1] Univ Vienna, Fac Life Sci, Dept Pharmaceut Chem, Althanstr 14, A-1090 Vienna, Austria

[2] Kaunas Univ Technol, Dept Organ Chem, Radvilenu Pl 19, LT-50254 Kaunas, Lithuania

[3] Kaunas Univ Technol, Inst Synthet Chem, K Barsausko G 59, LT-51423 Kaunas, Lithuania

来源：

BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY | 2018年 / 14卷

关键词：

dimerization; NMR (H-1; C-13; N-15); pyrazolones; X-ray structure analysis; thionyl chloride; PHOTOCHEMICAL OXIDATION; BIOLOGICAL-ACTIVITIES; HETEROCYCLIC-ANALOGS; PYRAZOLE; CHEMISTRY;

D O I：

10.3762/bjoc.14.110

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Dialkyl 5,5'-dioxo-4,4'-bipyrazole-4,4'-dicarboxylates are readily obtained by the reaction of 5-hydroxypyrazole-4-carboxylates in refluxing thionyl chloride. The obtained diesters can be transformed into the corresponding 4,4'-bipyrazoles via alkaline hydrolysis and subsequent decarboxylation. Detailed NMR spectroscopic investigations (H-1, C-13, N-15) were undertaken with all products prepared. Moreover, the structure of a representative 5,5'-dioxo-4,4'-bipyrazole-4,4'-dicarboxylate was confirmed by X-ray crystal structure analysis.

引用

页码：1287 / 1292

页数：6

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