Selective and reversible 1,3-dipolar cycloaddition of 6-aryl-1,5-diazabicyclo[3.1.0]hexanes with 1,3-diphenylprop-2-en-1-ones under microwave irradiation

Selective and reversible 1,3-dipolar cycloaddition of 6-aryl-1,5-diazabicyclo[3.1.0]hexanes with 1,3-diphenylprop-2-en-1-ones under microwave irradiation

The first example of the cycloaddition of in situ-generated azomethine imine under microwave conditions is described. The reaction of 6-aryl-1,5-diazabicyclo[3.1.0]hexanes with 1,3-diphenylprop-2-en-1-ones proceeds regio- and stereoselectively giving mostly good yields of the corresponding perhydrop...

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Veröffentlicht in:Beilstein journal of organic chemistry 2020-10, Vol.16 (1), p.2679-2686
Hauptverfasser: Molchanov, Alexander P, Efremova, Mariia M, Kryukova, Mariya A, Kuznetsov, Mikhail A
Format: Artikel
Sprache:eng
Schlagworte:
azomethine imines
Chemistry
cycloaddition
diazabicyclohexanes
diaziridines
Full Research Paper
regioselectivity
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Zusammenfassung:The first example of the cycloaddition of in situ-generated azomethine imine under microwave conditions is described. The reaction of 6-aryl-1,5-diazabicyclo[3.1.0]hexanes with 1,3-diphenylprop-2-en-1-ones proceeds regio- and stereoselectively giving mostly good yields of the corresponding perhydropyrazolopyrazoles. The products of the reaction undergo cycloreversion under the reaction conditions.
ISSN:1860-5397
1860-5397
DOI:10.3762/bjoc.16.218