ChemRxiv
These are preliminary reports that have not been peer-reviewed. They should not be regarded as conclusive, guide clinical practice/health-related behavior, or be reported in news media as established information. For more information, please see our FAQs.
RCCOM_dihydroquinolines_ChemRxiv.pdf (673.92 kB)
0/0

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

preprint
submitted on 09.12.2019 and posted on 17.12.2019 by 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.

Funding

Catalytic Platforms Using Aromatic Ions and Other Charged Species

National Institute of General Medical Sciences

Find out more...

History

Email Address of Submitting Author

thl36@cornell.edu

Institution

Cornell University

Country

United States of America

ORCID For Submitting Author

0000-0002-7720-3290

Declaration of Conflict of Interest

None

Exports

Logo branding

Categories

Exports