Selectivity of hydrogenations. Part 4 6- and 8-substituted quinaldines yield of tetrahydroderivatives and basicities of quinolines

Hönel, Michael; Vierhapper, Friedrich W.

doi:10.1007/bf00809353

Cited by 7 publications

(1 citation statement)

References 32 publications

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“…With these results, it is clear that varying the electronic nature of the substituent at either the 6- or the 7- position of the 3-formylquinolone affects its basicity [ 73 , 74 ], and therefore has a direct repercussion on the conversion during the Chan–Lam cross-coupling. Notwithstanding, a clear trend is not yet discernible; for that purpose, further experiments should be assessed varying the substituents on the quinolone core.…”

Section: Resultsmentioning

confidence: 99%

N-Arylation of 3-Formylquinolin-2(1H)-ones Using Copper(II)-Catalyzed Chan–Lam Coupling

et al. 2022

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3-formyl-2-quinolones have attracted the scientific community’s attention because they are used as versatile building blocks in the synthesis of more complex compounds showing different and attractive biological activities. Using copper-catalyzed Chan–Lam coupling, we synthesized 32 new N-aryl-3-formyl-2-quinolone derivatives at 80 °C, in air and using inexpensive phenylboronic acids as arylating agents. 3-formyl-2-quinolones and substituted 3-formyl-2-quinolones can act as substrates, and among the products, the p-methyl derivative 9a was used as a substrate to obtain different derivatives such as alcohol, amine, nitrile, and chalcone.

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Section: Resultsmentioning

confidence: 99%

N-Arylation of 3-Formylquinolin-2(1H)-ones Using Copper(II)-Catalyzed Chan–Lam Coupling

et al. 2022

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Regioselective Partial Hydrogenation and Deuteration of Tetracyclic (Hetero)aromatic Systems Using a Simple Heterogeneous Catalyst

Kehoe,

Lowry,

Light

et al. 2024

Chemistry A European J

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The introduction of added ‘3‐dimensionality’ through late‐stage functionalization of extended (hetero)aromatic systems is a powerful synthetic approach. The abundance of starting materials and cross‐coupling methodologies to access the precursors allows for highly diverse products. Subsequent selective partial reduction can alter the core structure in a manner of interest to medicinal chemists. Herein, we describe the precise, partial reduction of multicyclic heteroaromatic systems using a simple heterogeneous catalyst. The approach can be extended to introduce deuterium (again at late‐stage). Excellent yields can be obtained using simple reaction conditions.

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ChemInform Abstract: SELECTIVITY OF HYDROGENATIONS. PART 4. 6‐ AND 8‐SUBSTITUTED QUINALDINES. YIELD OF TETRAHYDRO DERIVATIVES AND BASICITIES OF QUINOLINES

Hoenel¹,

Vierhapper²

1985

Chemischer Informationsdienst

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Selectivity of hydrogenations. Part 4 6- and 8-substituted quinaldines yield of tetrahydroderivatives and basicities of quinolines

Cited by 7 publications

References 32 publications

N-Arylation of 3-Formylquinolin-2(1H)-ones Using Copper(II)-Catalyzed Chan–Lam Coupling

N-Arylation of 3-Formylquinolin-2(1H)-ones Using Copper(II)-Catalyzed Chan–Lam Coupling

Regioselective Partial Hydrogenation and Deuteration of Tetracyclic (Hetero)aromatic Systems Using a Simple Heterogeneous Catalyst

ChemInform Abstract: SELECTIVITY OF HYDROGENATIONS. PART 4. 6‐ AND 8‐SUBSTITUTED QUINALDINES. YIELD OF TETRAHYDRO DERIVATIVES AND BASICITIES OF QUINOLINES

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