Collect. Czech. Chem. Commun. 1993, 58, 2720-2728

Synthesis of Luminophoric Derivatives of PBD Based on 2,5-Diaryl Substituted Thiazoles and Oxazoles

Pavel Lhoták and Antonín Kurfürst

Department of Organic Chemistry, Prague Institute of Chemical Technology, 166 28 Prague 6, Czech Republic


The Friedel-Crafts acylation of 2-(biphenyl-4-yl)-5-phenyl-1,3,4-oxadiazole (PBD) with hippuryl chloride has been used to prepare the derivative V which on cyclization with POCl3 or P4S10 gives the respective oxazole (or thiazole) derivative of PBD, XIa or XIb. The reaction of carboxylic acid II with 4-(o-aminoacetyl)biphenyl in the presence of CDI gives N-acyl-α-aminoketone VII; the analogous compound VI has been prepared by acylating of o-aminoacetophenone with acyl chloride III. The cyclization of these compounds gives bifluorophores Xa - Xd.