1,3-dipolar cycloadditions of (4R,5R)-1-alkylidene-4-(benzoylamino)-5-phenyl-3-pyrazolidinon-1-azomethine imines

被引：14

作者：

Pezdirc, Lidija ^{[1
]}

Groselj, Uros ^{[1
]}

Meden, Anton ^{[1
]}

Stanovnik, Branko ^{[1
]}

Svete, Jurij ^{[1
]}

机构：

[1] Univ Ljubljana, Fac Chem & Chem Technol, Ljubljana 1000, Slovenia

来源：

JOURNAL OF HETEROCYCLIC CHEMISTRY | 2008年 / 45卷 / 01期

关键词：

D O I：

10.1002/jhet.5570450121

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

1,3-Dipolar cycloadditions of azomethine imines 3a and 3b, available by acid-catalyzed treatment of 3-pyrazolidinone 1 with acetone (2a) and butyraldehyde (2b), respectively, were studied. Reactions of 3a with DMAD (4) afforded a mixture of products 9 and 10a, whilst treatment of 3b with DMAD (4) gave a mixture of compound 9 and epimeric cycloadducts 10/10'b. On the other hand, cycloadducts 13a,b-16ab were isolated as single diastereomers in 9-37% yields upon reactions of 3a,b with olefinic dipolarophiles 5-8. The structures of cycloadducts 9,10a, 10/10'b, and 13a,b-16a,b were determined by H-1 nmr and NOESY spectroscopy. The structure of compound 13a was confirmed by X-ray diffraction.

引用

页码：181 / 188

页数：8

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← 1 2 3 4 5 6 →

1,3-dipolar cycloadditions of (4R*,5R*)-1-alkylidene-4-(benzoylamino)-5-phenyl-3-pyrazolidinon-1-azomethine imines

1,3-dipolar cycloadditions of (4R,5R)-1-alkylidene-4-(benzoylamino)-5-phenyl-3-pyrazolidinon-1-azomethine imines