An Innovative and Atom-Efficient Synthesis of Bioactive 2-Aroylfuran Derivatives Using Macroporous Polymer-Supported Cyanide

Abstract

A novel and safe approach was developed for the synthesis of bioactive 2-aroyl-3,5-diarylfurans in excellent yields by using a cyanide-impregnated anion-exchange resin as a versatile reagent. The possibility of reusing the polymer-supported reagent makes the process environmentally friendly and economically advantageous.

Key words

furans - green chemistry - ring contraction - hetero­cycles - nucleophilic additions

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• 15 Reaction of Triarylpyrylium Perchlorates 1 with Sodium Cyanide; General Procedure CAUTION: Cyanide salts can be absorbed through the skin and are extremely toxic. The appropriate triarylpyrylium perchlorate (1 mmol) was dissolved in MeCN (10 mL), NaCN (4 mmol) was added, and the mixture was refluxed until the reaction was complete. The solvent was then evaporated under vacuum, and the residue was adsorbed onto silica gel, which was mounted on a silica gel column and eluted with 20:80 Et₂O–hexane. The purified product was crystallized from EtOH.
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• 17 Polymer-Supported Cyanide Anion Amberlite IRA 910 (chloride ion form) was washed several times with distilled H₂O to remove foreign material. The dried resin (100 g) was then stirred with a soln of NaCN (32 g) in H₂O (450 mL) for 12 h. The cyanide solution was decanted, and the resin was washed with distilled H₂O until the washings gave a negative cyanide test (AgNO₃). The water was then decanted and replaced by the solvent to be employed as the reaction medium.
• 18 Estimation of the Capacity of the Polymer-Supported Cyanide A sample of resin-supported cyanide anion (1.00 g) was stirred for 12 h with KI (830 mg) in H₂O (10 mL). The resin was filtered off and washed several times with distilled H₂O. The combined filtrate and washings were titrated against 0.1 M aq AgNO₃ using a potentiometer. The capacity was generally found to be 1.4 mmol per gram of dry resin. Used resin could be readily regenerated by washing it sequentially with 1 M aq NaCl and aq NaCN.
• 19 Reaction of Triarylpyrylium Perchlorates 1 with Cyanide-Impregnated Anion-Exchange Resin; General Procedure The appropriate triarylpyrylium salt 1 (1 mmol) was stirred with the cyanide-impregnated Amberlite IRA 910 resin (4 mmol) in refluxing MeCN (10 mL) until the reaction was complete (TLC). The resin was then removed by filtration, and the filtrate was evaporated to give a crude product that was crystallized from EtOH.