Regioselective Passerini and Passerini-Knoevenagel Reactions with vic-Diketo Amides

The Passerini reaction of vic‐diketo amides with a variety of isocyanides and carboxylic acids has been examined. α‐Acyloxy β‐keto carboxamides were formed regioselectively as the major products. For the Passerini reactions with electron‐withdrawing‐group‐substituted acetic acids, a one‐pot Passerini–Knoevenagel reaction was accomplished by the addition of triethylamine. vic‐Diketo amides react with a variety of isocyanides and carboxylic acids in a regioselective Passerini three‐component reaction (P‐3CR) to give good to excellent yields of α‐acyloxy‐β‐keto‐carboxamides. In the case of Passerini reactions with electron‐withdrawing‐group‐substituted acetic acids, a one‐pot Passerini–Knoevenagel reaction was accomplished by the addition of triethylamine.