4.6 Article

One-pot construction of diverse and functionalized isochromenoquinolinediones by Rh(iii)-catalyzed annulation of unprotected arylamides with 3-diazoquinolinediones and their application for fluorescence sensor

Journal

RSC ADVANCES
Volume 9, Issue 30, Pages 17347-17357

Publisher

ROYAL SOC CHEMISTRY
DOI: 10.1039/c9ra03146d

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Funding

  1. National Research Foundation of Korea (NRF) - Korean government (MSIT) [2018R1A2B2004432]
  2. Priority Research Centers Program [2014R1A6A1031189]
  3. Korean Ministry of Education, Science and Technology [2012M3A7B4049675]

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A facile and efficient Rh(iii)-catalyzed annulation of arylamides with 3-diazoquinolinediones for the construction of diverse and highly functionalized isochromenoquinolinediones is described. Furthermore, the methodology is applicable for delivering various relevant molecules such as pyridopyranoquinolindiones, thienopyranoquinolinones, and indolopyranoquinolinone. The reaction proceeds via cascade C-H activation, carbene insertion, and intramolecular lactonization. The reaction exhibits high atom economy, good functional group tolerance, and high regioselectivity. The synthesized compound can also behave as a potent fluorescence sensor for Fe3+ ion.

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