One‐Pot and Regioselective Gold‐Catalyzed Synthesis of 2‐Imidazolyl‐1‐pyrazolylbenzenes from 1‐Propargyl‐1H‐benzotriazoles, Alkynes and Nitriles through α‐Imino Gold(I) Carbene Complexes
Advanced Synthesis and Catalysis(2016)
Abstract
A three‐component gold(I)‐catalyzed synthesis of 2‐imidazoyl‐1‐pyrazolylbenzenes from 1‐propargyl‐1H‐benzotriazoles is described here. Initially the benzotriazole derivative suffers an intramolecular 5‐endo‐dig cyclization to form a triazapentalene. This dipolar compound is able to perform an intermolecular and regioselective attack to a gold‐activated alkyne. After triazole breakage, the pyrazole ring and an α‐imino gold carbene complex are formed. Finally, the iminocarbene is captured by a nitrile to form an imidazole ring.
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Key words
alkynes,gold catalysis,imidazoles,iminocarbenes,pyrazoles
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