Synthesis of 1,2-Dihydroquinolines via Hydrazine-Catalysed Ring-Closing Carbonyl-Olefin Metathesis

17 December 2019, Version 1
This content is a preprint and has not undergone peer review at the time of posting.

Abstract

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.

Keywords

Carbonyl-olefin metathesis

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