title: Microwave assisted IMDAF# reaction: microwave irradiation applied with success to cycloaddition reaction of N-propargyl-N-p-tolyl-N-2-furfurylamines.
abstract: The new tertiary furfurylamine with triple bond as a dienophylic part i.e. N-(5-methyl-2-furfuryl)-N-prop-2-ynyl-p-toluidine (1) was prepared and the intramolecular Diels-Alder reaction of the amine (1) was performed under microwave irradiation conditions and by heating a benzene solution of the amine under nitrogen. Comparing the results of the usual thermal and the MAOS reaction, we confirmed our expectations that MAOS could promote the outcome of IMDA reaction of the suitably N-substituted tertiary 2-furfuryl-amines. In the present example, N-p-tolyl-5-methyl-5,7a-dihydro-5,7a-epoxyisoindoline was obtained in much better yield and of higher purity.
authors.affiliation: Faculty of Chemical Engineering and Technology, Department of Organic Chemistry, University of Zagreb, Marulićev trg 20, Zagreb, Croatia. admance@fkit.hr
authors.forename: Ana Dunja
authors.initials: AD
authors.lastname: Mance
authors.forename: Kresimir
authors.initials: K
authors.lastname: Jakopcić
mesh_terms: D003500:Cyclization / Q000528:radiation effects; D007202:Indicators and Reagents; D007211:Indoles / Q000737:chemistry; D008872:Microwaves; D008958:Models, Molecular; D008968:Molecular Conformation; D011084:Polycyclic Aromatic Hydrocarbons / Q000138:chemical synthesis / Q000737:chemistry* / Q000528:radiation effects; D014052:Toluidines / Q000737:chemistry
chemical_list: D007202:Indicators and Reagents; D007211:Indoles; D011084:Polycyclic Aromatic Hydrocarbons; D014052:Toluidines