Abstract
An efficient reduction of double bonds conjugated with nitrile groups and acid or base sensitive furan rings with 2-phenylbenzimidazoline generated in situ has been successfully accomplished with high yields and excellent selectivity. The employed reducing agent was prepared in one step from ordinary chemicals. The other advantages of the presented method include mild and convenient reaction conditions, a benign and cost effective reagent, simple work-up and separation of the products. As this process does neither affect cyano and nitro groups nor furan rings, it is a valuable alternative when metal-catalyzed hydrogenations or borohydride reductions have failed.
Highlights
Substituted furans are important and ubiquitous structural units present in large number of natural compounds [1], pharmaceuticals [1,2] and have been widely used as synthetic building blocks for the synthesis of many organic materials [3,4]
Despite the fact that a large group of reducing agents are used for reduction of conjugated unsaturated nitriles, only a limited number might be considered as really selective and accepted as being synthetically useful
The goal of the study was to find a suitable method for the chemoselective reduction of 3-phenyl, 3-(thiophen-2-yl) and 3-(5-substituted furan-2-yl)-2-cyanopropenenitriles 1a–g
Summary
Substituted furans are important and ubiquitous structural units present in large number of natural compounds [1], pharmaceuticals [1,2] and have been widely used as synthetic building blocks for the synthesis of many organic materials [3,4]. Despite the fact that a large group of reducing agents are used for reduction of conjugated unsaturated nitriles, only a limited number might be considered as really selective and accepted as being synthetically useful. To this group belong the so called organic hydride compounds
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