Journal
ORGANIC LETTERS
Volume 22, Issue 2, Pages 474-478Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acs.orglett.9b04233
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Funding
- National Research Foundation of Korea (NRF) - Korean government (MSICT) [NRF-2015R1A5A1008958, NRF-2019R1A2C2089953]
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Two distinctive transition-metal-promoted aerobic oxidation protocols have been developed for the synthesis of isoquinolones from 2-vinylbenzaldehydes and aniline derivatives. Thus, the one-pot tandem reaction sequence of imine formation, thermal 6 pi-electrocyclization, followed by either Cu(OAc)(2)-mediated or Pd(OAc)(2)-catalyzed aerobic oxidation protocol allowed the ready access to isoquinolone derivatives. The control experiments revealed that the 1,2-dihydroisoquinoline intermediates from the 6 pi-electrocyclization of 1-azatrienes were aerobically oxidized to isoquinolones in the presence of either Cu(OAc)(2) or Pd(OAc)(2) catalyst.
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