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Synthesis of 4-(1H-isochromen-1-yl)isoquinolines through the silver-catalysed homodimerization of ortho-alkynylarylaldehydes and subsequent condensation of the 1,5-dicarbonyl motif with NH₃
- Guo, Minghui, Meng, Xin, Zhao, Yang, Dong, Yuexia, Sun, Xuejun, Tian, Laijin, Cao, Ziping
- RSC advances 2019 v.9 no.5 pp. 2703-2707
- aldehydes, ammonia, carbonyl compounds, catalysts, isoquinolines, silver
- 4-(1H-Isochromen-1-yl)isoquinoline derivatives were synthesized in high yields via the AgBF₄-catalyzed self-reaction of ortho-alkynylarylaldehydes to give isochromene intermediates, followed by the dehydration of the 1,5-dicarbonyl motif with NH₃. Compared with electron-rich aromatic substituents, this strategy can provide the desired isochromene products with an electron-deficient isoquinoline unit. The reactions feature simple experimental operations, mild reaction conditions and high product yields.