Issue 55, 2016, Issue in Progress

Stoichiometry-controlled cycloaddition of nitrilimines with unsymmetrical exocyclic dienones: microwave-assisted synthesis of novel mono- and dispiropyrazoline derivatives

Abstract

Microwave-assisted 1,3-dipolar cycloaddition of (E,E)-1,3-bisarylidenetetral-2-ones with nitrilimines, generated in situ by dehydrohalogenation of the corresponding hydrazonoyl chlorides, affords a series of spiropyrazolines in good to excellent yields. The presence of a second exocyclic C[double bond, length as m-dash]C bond also allows the preparation of dispiropyrazolines. The cycloaddition proceeds with high chemo-, regio- and diastereoselectivity. The structure of the spiranic adducts has been established on the basis of their spectroscopic data and elemental analyses. The stereochemistry of these N-heterocycles has been confirmed by two X-ray diffraction studies. The luminescence properties and fluorescence quantum yields of these heterocyclic compounds have been investigated revealing that some of them are fluorescent in solution.

Graphical abstract: Stoichiometry-controlled cycloaddition of nitrilimines with unsymmetrical exocyclic dienones: microwave-assisted synthesis of novel mono- and dispiropyrazoline derivatives

Supplementary files

Article information

Article type
Paper
Submitted
14 Apr 2016
Accepted
09 May 2016
First published
11 May 2016

RSC Adv., 2016,6, 49868-49875

Stoichiometry-controlled cycloaddition of nitrilimines with unsymmetrical exocyclic dienones: microwave-assisted synthesis of novel mono- and dispiropyrazoline derivatives

H. Gazzeh, S. Boudriga, M. Askri, A. Khatyr, M. Knorr, C. Strohmann, C. Golz, Y. Rousselin and M. M. Kubicki, RSC Adv., 2016, 6, 49868 DOI: 10.1039/C6RA09703K

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