2H-Pyrano[3,2-c]quinolin-2-ones: their convenient synthesis and selected reactions

Čakurda, Matúš; Kois, Pavol; Addová, Gabriela; Lácová, Margita; Boháč, Andrej

doi:10.1007/s11696-017-0319-0

Cited by 5 publications

(2 citation statements)

References 8 publications

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“…Despite the interesting structure of vinyl-and alkenylquinolones, access to these molecules remains very restricted, limiting their use in organic synthesis. As far as we know, only a few studies have been carried out in this feld [22][23][24]. In 2012, Bach and coworkers reported the use of the Wittig reaction in the synthesis of some 3-vinyl-and 3-alkenyl-2quinolones from 3-formyl-2-quinolone.…”

Section: Introductionmentioning

confidence: 99%

“…In 2018, Boháč and coworkers described an efcient method for the synthesis of 2H-pyrano [3,2-c]quinolin-2-ones from 3formyl-4-quinolones and monosubstituted acetic acid. Te treatment of the obtained products with a solution of sodium hydroxide led to the formation of 3-(2-arylvinyl)-4-quinolones containing a carboxylic acid group at the β-position [24]. Based on these works, we envisioned that 3-formyl(quinoline and quinolones) (Figure 2) can be suitable substrates for the preparation of their corresponding highly conjugated 3-vinyl and 3-buta-1,3-dien-1-yl derivatives via Wittig reactions with nonstabilized ylides.…”

Section: Introductionmentioning

confidence: 99%

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Ultrasound-Assisted Wittig Reaction for the Synthesis of 3-Substituted 4-Chloroquinolines and Quinolin-4(1H)-ones with Extended π-Conjugated Systems

Frites

Khalfaoui

Hammal

et al. 2022

Journal of Chemistry

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3-(Vinyl-/buta-1,3-dien-1-yl/4-phenylbuta-1,3-dien-1-yl)-4-chloro quinolines and quinolin-4(1H)-ones were synthesized by ultrasound-assisted Wittig reaction of the corresponding 4-chloro-3-formylquinoline and 3-formylquinolin-4(1H)-ones with nonstabilized ylides. Ease execution, mild conditions, and high yields make this method exploitable for the generation of libraries of 3-substituted 4-chloroquinolines and quinolin-4(1H)-ones with extended π-conjugated systems. To demonstrate the usefulness of these compounds as precursors for the synthesis of more complex structures, 3-vinylquinolin-4(1H)-ones were used as dienes in the Diels–Alder reaction with N-methylmaleimide to produce novel acridone derivatives. The attempted Diels–Alder reaction with 3-(buta-1,3-dien-1-yl)quinolin-4(1H)-one did not afford the expected cycloadduct; instead, 2-methyl-2H-pyrano[3,2-c]quinoline was obtained. The structures and stereochemistry of the new compounds were established by NMR studies.

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Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Ultrasound-Assisted Wittig Reaction for the Synthesis of 3-Substituted 4-Chloroquinolines and Quinolin-4(1H)-ones with Extended π-Conjugated Systems

Frites

Khalfaoui

Hammal

et al. 2022

Journal of Chemistry

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Divergent Sequential Reactions of β‐(2‐Aminophenyl)‐α,β‐ynones with Malonyl Chloride

et al. 2022

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A viable one-pot synthesis of challenging 4H- [3,4-c]quinolone-4,5(6H)-diones by the reaction of β-(2-aminophenyl)-α,β-ynones with ethyl malonyl chloride is described. Their further elaboration in the presence of an excess of 40 % methyl amine aqueous solution in EtOH gives the benzo[c][2,7]naphthyridine-4,5(3H,6H)-diones of pharmacological interest in high yields.The product selectivity control of the divergent sequential condensation/C-annulation/intramolecular transesterification vs condensation/O-annulation/ring opening reactions of β-(2-aminophenyl)-α,β-ynones with malonyl chloride under metal free conditions has been addressed.

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Sequential condensation/biannulation reactions of β-(2-aminophenyl)-α,β-ynones with 1,3-dicarbonyls

et al. 2021

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2H-Pyrano[3,2-c]quinolin-2-ones: their convenient synthesis and selected reactions

Cited by 5 publications

References 8 publications

Ultrasound-Assisted Wittig Reaction for the Synthesis of 3-Substituted 4-Chloroquinolines and Quinolin-4(1H)-ones with Extended π-Conjugated Systems

Ultrasound-Assisted Wittig Reaction for the Synthesis of 3-Substituted 4-Chloroquinolines and Quinolin-4(1H)-ones with Extended π-Conjugated Systems

Divergent Sequential Reactions of β‐(2‐Aminophenyl)‐α,β‐ynones with Malonyl Chloride

Sequential condensation/biannulation reactions of β-(2-aminophenyl)-α,β-ynones with 1,3-dicarbonyls

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