Synthesis of Fused Pyrimidinone and Quinolone Derivatives in an Automated High-Temperature and High-Pressure Flow Reactor

• Published in: Journal of organic chemistry Vol. 82; no. 2; pp. 1073 - 1084
• Main Authors: Tsoung, Jennifer, Bogdan, Andrew R, Kantor, Stanislaw, Wang, Ying, Charaschanya, Manwika, Djuric, Stevan W
• Format: Journal Article
• Language: English
• Published: United States American Chemical Society 20-01-2017
• ISSN: 0022-3263; 1520-6904
• DOI: 10.1021/acs.joc.6b02520

Fused pyrimidinone and quinolone derivatives that are of potential interest to pharmaceutical research were synthesized within minutes in up to 96% yield in an automated Phoenix high-temperature and high-pressure continuous flow reactor. Heterocyclic scaffolds that are either hard to synthesize or require multisteps are readily accessible using a common set of reaction conditions. The use of low-boiling solvents along with the high conversions of these reactions allowed for facile workup and isolation. The methods reported herein are highly amenable for fast and efficient heterocycle synthesis as well as compound scale-ups.