Synthesis of C‑Ring-Substituted Vasicinones and Luotonins via Regioselective Aza-Nazarov Cyclization of Quinazolinonyl Enones

A facile synthesis of C-ring substituted luotonins and vasicinones has been realized via a super-acid-mediated aza-Nazarov cyclization of quinazolinonyl enones. The regioselectivity of the cyclization is highly dependent on proton availability in the reaction medium.

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Bibliographic Details
Published in:Organic letters 2019-12, Vol.21 (24), p.9824-9828
Main Authors: Rasapalli, Sivappa, Sammeta, Vamshikrishna Reddy, Murphy, Zachary F, Huang, Yanchang, Boerth, Jeffrey A, Golen, James A, Savinov, Sergey N
Format: Article
Language:English
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Summary:A facile synthesis of C-ring substituted luotonins and vasicinones has been realized via a super-acid-mediated aza-Nazarov cyclization of quinazolinonyl enones. The regioselectivity of the cyclization is highly dependent on proton availability in the reaction medium.
ISSN:1523-7060
1523-7052
DOI:10.1021/acs.orglett.9b03586