Amides reactions with alcohol

The use of Zn(OTf)2 with a Ru complex, TpRuPPh3(MeCN)2PF6, proved useful for the cyclization of propargyl alcohols 99 with amides. The reaction proceeded through the intermediate 100 which was also isolated from the reaction mixture when only the Zn catalyst was used. Upon heating with the mixture of the two catalysts, compound 100 was completely converted into the final oxazole 101 <06JOC4951>. 

On the other hand, TMSOTf activates acetoxybenziodazoles to afford 3-iminobenziodoxoles upon reaction with amides and alcohols via an acid-catalyzed rearrangement (eq 105). ... 

Acidity of Amides, Imides, and Sulfonamides Characteristic Reactions Reaction with Water Hydrolysis Reaction with Alcohols Reactions with Ammonia and Amines Reaction of Acid Chiorides with Salts of Carboxylic Acids Interconversion of Functional Derivatives Reactions with Organometallic Compounds 18.10 Reduction... 

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