Tetrahedron p. 6211 - 6220 (1989)
Update date:2022-08-02
Topics:
Biedrzycki, Marek
Bie, Dick A. de
Plas, Henk C. van der
Thermally induced intramolecular Diels-Alder cyclisations of (alkynyloxyalkyl)pyrazines to dihydropyranopyridines have been studied in the solvent undecane.The introduction of a phenyl group in the α-position of the 3-butynyloxymethyl side chain leads to a 3-4 fold increase of the reaction rate, while the influence of a γ-phenyl group on the rate is negligible.The (3-butynyloxymethyl)pyrazine reacts about 7 times slower than the (3-propynyloxyethyl)pyrazine; the presence of a trimethylsilyl group at the terminus of the alkyne decreases in general the rate of the intramolecular cyclisation.The mechanisms are discussed.
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