ABSTRACT
A study was conducted to gain insight into the preparative potential of photosensitized reactions of acyclic N-benzylglycinates containing an α-trimethylsilyl group with dimethyl acetylenedicarboxylate (DMAD). The photosensitizers employed in the reactions include 9,10-dicyanoanthracene (DCA), 1,4-dicyanonaphthalene (DCN), rose bengal (RB) and fullerene C60. The results show that photoirradiation of oxygenated solutions containing the photosensitizers, glycinates and dimethyl acetylenedicarboxylate leads to competitive formation of pyrroles and ß-enamino-esters. The distributions of pyrrole and ß-enamino-ester products formed in these reactions are highly influenced by the electronic nature of the phenyl ring substituent on the benzylglycinates and the photosensitizer used. These photoaddition reactions take place via mechanistic pathways involving competitive formation of azomethine ylides and secondary amines, generated by a mechanistic routes involving initial SET from the benzylglycinates to photosensitizers.
ABSTRACT
A series of diverse polyfunctionalized triheterocyclic benzothiazoles were easily prepared in excellent yields via the Biginelli reaction of 2-aminobenzothiazole with substituted benzaldehydes and α-methylene ketones using FeF(3) as an expeditious catalyst under solvent-free conditions. The protocol provides a practical and straightforward approach toward highly functionalized triheterocyclic benzothiazole derivatives in excellent yields. The reaction was conveniently promoted by FeF(3) and the catalyst could be recovered easily after the reaction and reused without any loss of its catalytic activity. The advantageous features of this methodology are high atom economy, operational simplicity, shorter reaction time, convergence, and facile automation.
