Pyrimidine ortho-quinodimethanes. Part 2: Synthesis of new [60]fullerene adducts based on substituted pyrimidine derivatives and their super(1)H NMR dynamic study

The Diels-Alder reaction of various pyrimidine ortho-quinodimethanes generated in situ with C sub(60) gives access to a variety of new fullerodihydroquinazoline derivatives. This variety is increased since substituents on the pyrimidine ring can be easily modified before or after its reaction with C...

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Bibliographic Details
Published in:Tetrahedron 2009-07, Vol.65 (29-30), p.5817-5823
Main Authors: Herrera, Antonio, Martinez-Alvarez, Roberto, Martin, Nazario, Chioua, Mourad, Chioua, Rachid, Molero, Dolores, Sanchez-Vazquez, Angel, Almy, John
Format: Article
Language:English
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Summary:The Diels-Alder reaction of various pyrimidine ortho-quinodimethanes generated in situ with C sub(60) gives access to a variety of new fullerodihydroquinazoline derivatives. This variety is increased since substituents on the pyrimidine ring can be easily modified before or after its reaction with C sub(60). Variable temperature super(1)H NMR spectra provided thermodynamic parameters related to the boat-to-boat interconversion of the cyclohexene ring fused to the fullerene moiety. The mass spectra of the prepared cycloadducts show that the retro-Diels-Alder process takes place easily with elimination of the corresponding diene molecule.
ISSN:0040-4020
DOI:10.1016/j.tet.2009.05.026