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RCCOM_dihydroquinolines_ChemRxiv.pdf (673.92 kB)
Synthesis of 1,2-Dihydroquinolines via Hydrazine-Catalysed Ring-Closing Carbonyl-Olefin Metathesis
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submitted on 09.12.2019 and posted on 17.12.2019by Yunfei Zhang, Jae Hun Sim, Samantha N. Macmillan, Tristan Lambert
The synthesis of 1,2-dihydroquinolines by the
hydrazine-catalysed ring-closing carbonyl-olefin metathesis (RCCOM) of
N-prenylated 2-aminobenzaldehydes is reported. Substrates with a variety of
substitution patterns are shown, and the compatibility of these conditions with
a range of additives is demonstrated.
With an acid-labile protecting group on the nitrogen atom, in situ
deprotection and autoxidation furnishes quinolines. In comparison to related oxygen-containing
substrates, the cycloaddition step of the catalytic cycle is shown to be
slower, but the cycloreversion is found to be more facile.