Original scientific paper

On the Preparation of Some Tertiary Amines Containing the 2-Furfuryl Group. Isomerization of Allyl-aryl( 2-furfuryl)-amines to N-Aryl-4H-5, 7 a-epoxyisoindolines

D. Bilović ; Department of Organic Chemistry and Biochemistry, Institute »Ruder Boskovic«
V. Hahn ; Laboratory of Organic Chemistry, Faculty of Technology, University of Zagreb, Zagreb, Croatia, Yugoslavia

Abstract

Six new tertiary 2-furfurylamines of the general formula
2-C 4H 30 · CH2 NRAr, w h ere R represents methyl, ethyl or ally!,
and Ar phenyl, p-tolyl or p-methoxyphenyl groups, have been prepared
by alkylation of the appropriate secondary aryl-(2-furfuryl)-
amines with alkyl or ally! halides.
It was found that the oily allyl-aryl-(2-furfuryl)-amines, on
standing at room temperature, spontaneously isomerized to crystalline
N-aryl-4H-5,7a-epoxyisoindolines, formed by a reversible intramolecular
Diels-Alder reaction.

Keywords

Hrčak ID:

208085

URI

https://hrcak.srce.hr/208085

Publication date:

15.10.1967.

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