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. Issue 9 (17th March 2016)

• Record Type: Journal Article
• Authors: González, Jairo; Santamaría, Javier; Suárez‐Sobrino, Ángel L.; Ballesteros, Alfredo
• Is Part Of: Advanced synthesis & catalysis. Volume 358:Issue 9(2016)
• Page Start: 1398
• Page End: 1403
• Publication Date: 2016-03-17
• Subjects: alkynes -- gold catalysis -- imidazoles -- iminocarbenes -- pyrazoles; Catalysis -- Periodicals; Organic compounds -- Synthesis -- Periodicals; Chemistry -- Periodicals; Chemistry, Technical -- Periodicals; Chemistry -- Periodicals; Catalysis -- Periodicals; Technology, Pharmaceutical -- Periodicals; 547.2
• DOI: 10.1002/adsc.201600022
• Languages: English
• ISSNs: 1615-4150

Abstract

Abstract: A three‐component gold(I)‐catalyzed synthesis of 2‐imidazoyl‐1‐pyrazolylbenzenes from 1‐propargyl‐1 H ‐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. Abstract :