Reinvestigation of the synthesis of 3-dimethylallyl-4-hydroxy-2-quinolones. A novel route to tetracyclic heteroaromatic compounds

doi:10.1039/P19770002546

Paper

Reinvestigation of the synthesis of 3-dimethylallyl-4-hydroxy-2-quinolones. A novel route to tetracyclic heteroaromatic compounds

Published Mar 14, 1978 · R. Oels, R. Storer, D. W. Young

Journal of The Chemical Society-perkin Transactions 1

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Abstract

The reaction of diethyl 2-(3-methylbut-2-enyl)malonate with a variety of anilines has been used in the past as a method of alkaloid synthesis. It has now been found that this reaction yields, in addition to the expected 3-di methylallyl-4-hydroxy-2-quinolones, 3,3′-methylenebis -4-hydroxy-2-quinolones, and dibenzo[b,h][1,6]naphthyridin-6(5H)-ones. A mechanism is suggested to explain this unusual reaction.

Study Snapshot

The reaction of diethyl 2-(3-methylbut-2-enyl)malonate with anilines yields not only 3-dimethylallyl-4-hydroxy-2-quinolones but also 3,3′-methylenebis-4-hydroxy-2-quinolones and dibenzo[b,h

PopulationOlder adults (50-71 years)

Sample size24

MethodsObservational

OutcomesBody Mass Index projections

ResultsSocial networks mitigate obesity in older groups.

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Paper

Reinvestigation of the synthesis of 3-dimethylallyl-4-hydroxy-2-quinolones. A novel route to tetracyclic heteroaromatic compounds

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References

Citations

Ligand-free palladium-catalyzed facile construction of tetra cyclic dibenzo[b,h][1,6]naphthyridine derivatives: domino sequence of intramolecular C–H bond arylation and oxidation reactions

Ligand-free palladium-catalyzed approach enables facile synthesis of dibenzo-fused naphthyridines, with a domino sequence of C-H functionalization and oxidation reactions, applicable to a wide range of substrates.

One-pot synthesis of dibenzo[b,h][1,6]naphthyridines from 2-acetylaminobenzaldehyde: application to a fluorescent DNA-binding compound.

This one-pot synthesis of dibenzo[b,h][1,6]naphthyridines from 2-acetylaminobenzaldehyde can produce fluorescent DNA-binding compounds with strong fluorescence, which can be changed by intercalation into double-stranded DNA

Efficient palladium-catalyzed direct arylation of azines and diazines using ligand-free conditions

Palladium-catalyzed direct arylation effectively produces polyazacyclic systems using ligand-free conditions, providing various products from regioselective coupling.

Chapter 5 Quinoline Alkaloids Related to Anthranilic Acid

Quinoline alkaloids, derived from anthranilic acid, have shown significant progress in isolation, synthesis, and structure elucidation, with potential applications in various fields.