Ammonium Acetate Catalyzed Formation of 1,5‐Benzodiazepines through [4+2+1] Cycloaddition Involving 5‐Hydroxymethylfurfural

The use of the renewable platform molecule 5-hydroxymethylfurfural (5-HMF) in multi-component reaction with a diamine and an alkynone to generate seven-membered 1,5-benzodiazepines is described. Due sensitivity 5-HMF strong acidic basic conditions, investigation required in-depth revisit parameters as compared benchmark aldehydes. Among catalysts/solvents couples, ammonium acetate ethanol proved be clean efficient system. These optimized conditions were subsequently used investigate scope providing library moderate good yields from wide range diversely substituted diamines alkynones or alkyl alkynoates.