Phenacylfurans having a furan ring capable of transformation and a carbonyl group are interesting subjects for a study of their chemical reactions. Several methods are known for the synthesis of this group of compounds [1-6] but the methods have certain restrictions.For preparation of phenacylfurans we propose the use of a radical substitution method which has undergone a rapid expansion in recent years, primarily thanks to the development of preparative methods for generating free radicals. In particular, there is a report in the literature of the radical alkylation of furan and 2-methylfuran by ethyl iodoacetate in the presence of the Fenton's reagent (H 2 O 2 / FeSO 4 in DMSO) [7,8]. It should be noted that the most popular reagents for radical alkylation are both iodides and xanthates [9]. With the availability of phenacyl xanthates 1 [9] in mind we have studied their reactivity towards 2-methylfuran in the presence of the Fenton's reagent and obtained the target compounds 2 in quite reasonable yields. O R S S OEt O Me O R O Me + H 2 O 2 / FeSO 4 DMSO 1a-c 2a-c 1, 2 a R = OMe, b R = Br, c R = NO 2Hence we have shown that phenacyl xanthates can alkylate 2-methylfuran in the presence of Fenton's reagent in preparative yields. The simplicity of carrying out the reaction and the availability of the starting materials make this route a valuable alternative to the existing methods for the preparation of phenacylfurans.
Treatment of 1-(2-isothiocyanoaryl)-2-(2-furyl)ethane with anhydrous aluminum chloride under Friedel-Crafts conditions yielded a pyrrolo[1,2-a]quinoline derivative via electrophilic attack of the activated isothiocyano group onto the furan ring. The analogous diarylethane under these conditions underwent intramolecular cyclization leading to an eight-membered thioamide.
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