One-Pot and Regioselective Gold-Catalyzed Synthesis of 2-Imidazolyl-1-pyrazolylbenzenes from 1-Propargyl-1H-benzotriazoles, Alkynes and Nitriles through [alpha]-Imino Gold(I) Carbene Complexes

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 interm...

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Bibliographic Details
Published in:Advanced synthesis & catalysis 2016-04, Vol.358 (9), p.1398
Main Authors: Gonzalez, Jairo, Santamaria, Javier, Suarez-Sobrino, Ángel L, Ballesteros, Alfredo
Format: Article
Language:English
Subjects:
Alkynes
Benzotriazole
Breakage
Chemical synthesis
Gold
Imidazole
Nitriles
Pyrazole
Regioselectivity
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Summary: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 [alpha]-imino gold carbene complex are formed. Finally, the iminocarbene is captured by a nitrile to form an imidazole ring.
ISSN:1615-4150
1615-4169
DOI:10.1002/adsc.201600022