Efficient synthesis of novel benzo[b][1,8]naphthyridin-4(1H)-ones and pyrido[2,3-b]quinoxalin-4(1H)-ones from alkynones and primary amines

Iaroshenko, Viktor O.; Zahid, Muhammad; Mkrtchyan, Satenik; Gevorgyan, Ashot; Altenburger, Kai; Knepper, Ingo; Villinger, Alexander; Sosnovskikh, Vyacheslav Ya.; Langer, Peter

doi:10.1016/j.tet.2013.01.008

Cited by 10 publications

(6 citation statements)

References 24 publications

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“…The reaction of 2-chloroquinoxaline-3-carboxylic acid ( 34a ) with thionyl chloride gave the acid chloride 34b (Scheme 13 ). 18 Sonogashira reaction of the latter with three alkynes afforded ynones 35a – c in moderate yields. Cyclization of 35a – c with various amines afforded pyrido[2,3- b ]quinoxalin-4-ones 36a – n in good to excellent yields.…”

Section: Domino C–n Coupling/hydroamination Reactionsmentioning

confidence: 99%

Synthesis of Nitrogen Heterocycles by Domino C–N Coupling/Hydroamination Reactions

Langer

2022

Synlett

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The present article presents a personalized Account on the synthesis of nitrogen heterocycles by domino C–N coupling/hydroamination reactions and related processes. The starting materials, 2-alkynyl-1-halohetarenes, are regioselectively available by Sonogashira reactions of various 1,2-dihalogenated heterocycles, such as thiophenes, benzothiophenes, furans and benzofurans, pyridines, quinolines, pyrimidines, and other ring systems. More complex products are formed by domino C–N coupling/hydroamination/C–H arylation reactions of 2-alkynyl-1-halohetarenes with 2-bromoanilines. In these reactions, not only two, but three bonds are formed in one step. In many cases, the products constitute new heterocyclic core structures and show interesting pharmacological or fluorescence properties.1 Introduction2 Domino C–N Coupling/Hydroamination Reactions3 Domino C–N Coupling/Hydroamination/C–H Arylation Reactions4 Conclusions

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Section: Domino C–n Coupling/hydroamination Reactionsmentioning

confidence: 99%

Synthesis of Nitrogen Heterocycles by Domino C–N Coupling/Hydroamination Reactions

Langer

2022

Synlett

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“…Similarly, the reaction of 1-(2-chloropyridin-3-yl)prop-2-yn-1-ones (70) and 2 equiv of amines in the presence of 2 equiv of K 2 CO 3 in DMF afforded the corresponding enaminoketone intermediates (71), which cyclized to produce 1,8-naphthyridin-4(1H)-ones (72) with the elimination of amine (Scheme 40). 65 In the case of arylamines, the cyclization proceeded in low yields (18%-29%).…”

Section: 4-addition Of Amines and Nucleophilic Aromatic Substitutionmentioning

confidence: 99%

“…Compounds 80 were cyclized by S N Ar reaction to give benzo[b]-1,8-naphthyridin-4(1H)-ones (81) with the elimination of amine (Scheme 44). 71 The reaction of 2 0 -fluoro(bromo)alkynones (82) and aliphatic primary amines in EtOH/THF (1/1, v/v) afforded the corresponding 1,4-addition products (83). After solvents removal by evaporation, compounds 83 were treated with sodium hydride in DME at 25 C and heated at 80 C to give 1-alkyl-2-phenyl-4-quinolones (84) readily by S N Ar reaction (Scheme 45).…”

Section: 4-addition Of Amines and Nucleophilic Aromatic Substitutionmentioning

confidence: 99%

A review of the syntheses of (thio)flavones, 4‐quinolones, (thio)aurones, and azaaurones from 2′‐substituted alkynones

Lee

2021

Bulletin Korean Chem Soc

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Flavones have been prepared by the 6-endo cyclization of o-alkynoylphenols, cyclization/deprotection of 2 0 -protected alkynones, or carbonylative coupling of 2-halophenols with arylacetylenes and subsequent cyclization. (Z)-Aurones have been prepared by the 5-exo cyclization of o-alkynoylphenols or oxidation of (Z)-benzylidenebenzofuran-3-ols with MnO 2 . Thioflavones have been prepared by deprotection/6-endo cyclization of S-protected alkynones or by the addition of sulfur to 2 0 -halo(methoxy)alkynones and subsequent cyclization. Deprotection and 5-exo cyclization of S-benzylated alkynones using HCOOH afforded (Z)-thioaurones. 2-Phenyl-4-quinolones have been prepared by the 6-endo cyclization of 2 0 -aminoalkynones or by the addition of amines to 2 0haloalkynones and subsequent cyclization. Furthermore, the treatment of 2 0aminoalkynones with triphenylphosphine afforded (Z)-azaaurones by 5-exo cyclization.

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“…A catalyst‐free approach has been recorded for the synthesis of 4‐quinolones. Here F, Cl, Br, and NO 2 acted as good leaving groups under base‐promoted conditions. In this regard, a use of palladium catalyst was able to lower the reaction temperature .…”

Section: Nitrogen‐containing Nucleophilesmentioning

confidence: 99%

“…Here F, Cl, Br, and NO 2 acted as good leaving groups under base‐promoted conditions. In this regard, a use of palladium catalyst was able to lower the reaction temperature . Besides, the addition of ( R )‐MOP‐Pd 2 (dba) 3 catalyst enabled the enantioselective synthesis of 2‐aryl‐4‐quinolinone derivatives (Scheme ).…”

Section: Nitrogen‐containing Nucleophilesmentioning

confidence: 99%

Tandem Reactions of Ynones: via Conjugate Addition of Nitrogen‐, Carbon‐, Oxygen‐, Boron‐, Silicon‐, Phosphorus‐, and Sulfur‐Containing Nucleophiles

et al. 2019

Adv Synth Catal

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Scheme 12. Enamines:T BAF-catalyzed cyclization.Scheme 13. Intramolecular cyclization.Scheme14. Intramolecular cyclizations.Scheme15. CÀNa nd OÀNb ond cleavage. Scheme 16. Applications of RNH-Nu. Scheme 17. NH-sulfoximines and NH-sulfondiimines. Scheme18. Radical cyclizationf or the synthesis of indoles. Scheme 22. 2H-Azirines:[3 + +2] cycloadditions. Scheme 23. Visible light-induced cycloaddition for pyrrole synthesis. Scheme24. Cyclization and sulfonyl migration. Scheme 25. NR 2 -E strategy analysis. Scheme 57. Several arenes for annulations. Scheme 58. Conjugateaddition. Scheme 59. Asymmetric conjugate addition.Scheme60. Conjugatea ddition andcyclization.

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Efficient synthesis of novel benzo[b][1,8]naphthyridin-4(1H)-ones and pyrido[2,3-b]quinoxalin-4(1H)-ones from alkynones and primary amines

Cited by 10 publications

References 24 publications

Synthesis of Nitrogen Heterocycles by Domino C–N Coupling/Hydroamination Reactions

Synthesis of Nitrogen Heterocycles by Domino C–N Coupling/Hydroamination Reactions

A review of the syntheses of (thio)flavones, 4‐quinolones, (thio)aurones, and azaaurones from 2′‐substituted alkynones

Tandem Reactions of Ynones: via Conjugate Addition of Nitrogen‐, Carbon‐, Oxygen‐, Boron‐, Silicon‐, Phosphorus‐, and Sulfur‐Containing Nucleophiles

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