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Issue 5, 2019
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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

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Abstract

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.

Graphical abstract: 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

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Publication details

The article was received on 09 Nov 2018, accepted on 07 Jan 2019 and first published on 21 Jan 2019


Article type: Paper
DOI: 10.1039/C8RA09269A
RSC Adv., 2019,9, 2703-2707
  • Open access: Creative Commons BY-NC license
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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

    M. Guo, X. Meng, Y. Zhao, Y. Dong, X. Sun, L. Tian and Z. Cao, RSC Adv., 2019, 9, 2703
    DOI: 10.1039/C8RA09269A

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