A Facile Synthesis of 4,6,7,8,8 a ,9‐Hexahydropyrrolo[1,2‐ a ][1,2,3]triazolo[1,5‐ d ]pyrazines by a Three‐Component Coupling Reaction Followed by Intramolecular 1,3‐Dipolar Cycloaddition

A practical and efficient two‐step protocol for the synthesis of several new 4,6,7,8,8 a ,9‐hexahydropyrrolo[1,2‐ a ][1,2,3]triazolo[1,5‐ d ]pyrazines is described. The first step involves the AuBr 3 ‐catalyzed three‐component coupling reaction of terminal alkynes, aldehydes, and amines under solvent‐free conditions to provide the requisite propargylamines. The reaction tolerates a high structural diversity, requires only short reaction times, gives high diastereoselectivities, and is environmentally benign. Furthermore, the propargylamine products undergo catalyst‐free intramolecular azide–alkyne [3 + 2] dipolar cycloaddition reactions to give the 4,6,7,8,8 a ,9‐hexahydropyrrolo[1,2‐ a ][1,2,3]triazolo[1,5‐ d ]pyrazines in excellent yields and with excellent diastereoselectivities.