Microwave assisted IMDAF# reaction: microwave irradiation applied with success to cycloaddition reaction of N-propargyl-N-p-tolyl-N-2-furfurylamines.
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.
Mance
Ana Dunja
AD
Faculty of Chemical Engineering and Technology, Department of Organic Chemistry, University of Zagreb, Marulićev trg 20, Zagreb, Croatia. admance@fkit.hr
Jakopcić
Kresimir
K
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
D007202:Indicators and Reagents; D007211:Indoles; D011084:Polycyclic Aromatic Hydrocarbons; D014052:Toluidines