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- Title
Silver Triflate-Palladium Chloride Cooperative Catalysis in a Tandem Reaction for the Synthesis of H-Pyrazolo[5,1- a]isoquinolines.
- Authors
Xiao, Qing; Sheng, Jie; Ding, Qiuping; Wu, Jie
- Abstract
A tandem reaction of N′-(2-alkynylbenzylidene)hydrazone with alcohol in the presence of oxygen co-catalyzed by silver triflate and palladium chloride under mild conditions is reported, providing H-pyrazolo[5,1- a]isoquinolines in good yields. During the transformation, isoquinolinium-2-yl amide was the key intermediate via a silver(I)-catalyzed 6- endo cyclization of N′-(2-alkynylbenzylidene)hydrazone. The presence of a palladium catalyst and molecular oxygen promoted the oxidation of the alcohol to the aldehyde or ketone. Subsequent nucleophilic attack of the in situ generated enolate to isoquinolinium-2-yl amide, intramolecular condensation, and aromatization afforded the H-pyrazolo[5,1- a]isoquinolines. The easily available starting materials, good substrate generality, mild reaction conditions, and experimental ease should make this method attractive for further library construction.
- Subjects
ISOQUINOLINE synthesis; SILVER compounds; CATALYSIS; CHEMICAL reactions; OXYGEN; RING formation (Chemistry)
- Publication
Advanced Synthesis & Catalysis, 2013, Vol 355, Issue 11/12, p2321
- ISSN
1615-4150
- Publication type
Article
- DOI
10.1002/adsc.201300327