Journal
ORGANIC & BIOMOLECULAR CHEMISTRY
Volume 13, Issue 48, Pages 11657-11662Publisher
ROYAL SOC CHEMISTRY
DOI: 10.1039/c5ob01972a
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Funding
- National Natural Science Foundation of China [21372046]
- Science & Technology Commission of Shanghai Municipality [12JC1403800]
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A silver(I)-catalyzed reaction of (1-arylethylidene) hydrazides with N'-(2-alkynylbenzylidene) hydrazides is reported, which provides an efficient approach for the synthesis of pyrazolo[5,1-a]isoquinolines. During the reaction process, azo-alkene and isoquinolinium-2-yl amide acted as the key intermediates, which then underwent [3 + 2] cycloaddition and intramolecular rearrangement leading to the corresponding pyrazolo[5,1-a] isoquinolines. Azo-alkene would be formed in situ from (1-arylethylidene) hydrazide in the presence of I-2 and TBHP, and isoquinolinium-2-yl amide would be generated in situ via a silver(I)promoted 6-endo cyclization of N'-(2-alkynylbenzylidene) hydrazide. This transformation proceeds smoothly under mild conditions and tolerates a broad range of functional groups.
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