Acid-Catalyzed [3+2] Cycloaddition of Enones with Azomethine Imines for Easy Access to Tetrahydropyrazolopyrazolones

Aluminum chloride (AlCl3) or zirconium chloride (ZrCl4) catalyzes efficiently the [3+2] cycloaddition of N, N'-cyclic azomethine imines with enones which contain the vinyl group. The scope of the reaction towards various azomethine imines and enones has been explored. Access to diastereomerical...

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Bibliographic Details
Published inSynlett Vol. 28; no. 6; pp. 664 - 668
Main Authors Jovanovic, Jovana P., Bogdanovic, Goran A., Damljanovic, Ivan
Format Journal Article
LanguageEnglish
Published STUTTGART Thieme Medical Publishers 01.04.2017
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
Lewis acid
ANNULATION
COMPLEXES
dipolar cycloaddition
PYRAZOLIDINONES
YLIDES
FACILE ACCESS
HETEROCYCLES
ALLENOATES
ESTERS
N,N '-bicyclic heterocycles
N,N '-cyclic azomethine imine
ENANTIOSELECTIVE 1,3-DIPOLAR CYCLOADDITION
enone
AMIDES
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Summary:Aluminum chloride (AlCl3) or zirconium chloride (ZrCl4) catalyzes efficiently the [3+2] cycloaddition of N, N'-cyclic azomethine imines with enones which contain the vinyl group. The scope of the reaction towards various azomethine imines and enones has been explored. Access to diastereomerically pure 6-acyl-5-aryltetrahydropyrazolo[1,2-a] pyrazol-1(5H)-ones is provided by easy chromatographic separations.
ISSN:0936-5214
1437-2096
DOI:10.1055/s-0036-1588678