Chemoselective cascade synthesis of N-fused heterocycles via silver(I) triflate-catalyzed friedel-crafts/N-C bond formation sequence

Advanced Synthesis and Catalysis

Volumn 352, Issue 18, 2010, Pages 3215-3222

  Hao, Lu ^a   Pan, Yingming ^a   Wang, Tao ^a   Lin, Min ^a   Chen, Li ^a   Zhan, Zhuang Ping ^a  

^a XIAMEN UNIVERSITY   (China)

Author keywords

cascade reaction; Friedel Crafts reaction; indoles; N fused heterocycles; propargyl alcohol; silver

Indexed keywords

EID: 78650374372     PISSN: 16154150     EISSN: 16154169     Source Type: Journal    
DOI: 10.1002/adsc.201000525     Document Type: Article

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76. The experiments on capturing the three key intermediates are performed with propargyl alcohols 1 (0.5 mmol, 1.0 equiv.), 3-substituted indoles 2 (0.55 mmol, 1.1 equiv.) and 5 mol% AgOTf (0.025 mmol) in toluene (2 mL), which are shown below. In the course of forming 6, 7 and 8, certain amounts of the corresponding final N-fused heterocycles (3aa, 4ha and 5ja) were also furnished. Without isolation and after being heated for an appropriate time, these intermediates would be converted completely into corresponding N-fused heterocyclic products.