An improved synthesis of the alkaloid Luotonin-A employing ionic liquid and water as key solvents

Effective and Sustainable Access to Quinolines and Acridines: A Heterogeneous Imidazolium Salt Mediates C–C and C–N Bond Formation

“…Methyl 2‐Methylquinoline‐3‐carboxylate (3bc): Pale yellow solid; purification by column chromatography (hexane/ethyl acetate, 8.0:2.0), 75 % yield; m.p. : 57–59 °C (AcOEt) [Lit.…”

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

“…This increased attention is partly due to toxic side effects associated with the hydrolyzable lactone E -ring of CPT that could be alleviated with luotonin’s highly stable benzo E -ring. To date, several reports have appeared on total synthesis and structural modifications of luotonin A in an effort to find a more potent lead. , The synthetic modifications reported thus far on the luotonin A core include principally alkyl and haloalkyl substituents on the A-ring; , aryl, alkyl, aminoalkyl, and trifluoromethyl substituents on the B-ring; and halo, trifluoromethyl, and phenyl substituents on the E-ring …”

Total Synthesis of Luotonin A and Rutaecarpine from an Aldimine via the Designed Cyclization

“…Since rutaecarpine ( 1 ) and luotonin A ( 2 ) (Scheme ) display a wide range of interesting biological activities, not surprisingly, numerous synthetic endeavors have been made toward the total syntheses of these natural products. − Despite the fact that these two natural products belong to the same family of quinazolinone alkaloids, most of the previous syntheses of these natural products have been accomplished via independent synthetic routes that utilize starting materials bearing different skeletal frameworks. The synthesis of these two quinazolinone alkaloids from a common intermediate has not been reported to date .…”