Efficient Syntheses of Fluorine-Containing Pyrimido[5,4-c]quinolines and Benzo[h][1,6]naphthyridines by Condensation Reactions of 3-Trifluoro-acetylquinolin-4-amine with Aldehydes and Ketones

Okada, Etsuji; Hatakenaka, Mizuki; Nakano, Shiro

doi:10.3987/com-14-13070

Cited by 4 publications

(4 citation statements)

References 27 publications

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“…Further dehydrogenation of dihydropyrimido [5,4-c]quinolines 205a-n, utilizing 4,5-dichloro-3,6-dioxocyclohexa-1,4-diene-1,2-dicarbonitrile (DDQ), resulted in the formation of pyrimido [5,4-c]quinolines 206a-n (Scheme 28). [43] In contrast, when ketones 209 were employed instead of aldehydes under nearly identical conditions, predominantly benzo[h] [1,6]naphthyridine derivatives 210a,b were obtained in excellent combined yields. Additionally, some ketones led to the formation of pyrimido [5,4-c]quinolines 211a,b under the same reaction conditions (Scheme 29).…”

Section: From 4-haloquinolinementioning

confidence: 99%

“…Additionally, some ketones led to the formation of pyrimido [5,4-c]quinolines 211a,b under the same reaction conditions (Scheme 29). [43] Scheme 25. Synthesis of pyrimido [5,4-…”

Section: From 4-haloquinolinementioning

confidence: 99%

“…Further dehydrogenation of dihydropyrimido[5,4‐ c ]quinolines 205a – n , utilizing 4,5‐dichloro‐3,6‐dioxocyclohexa‐1,4‐diene‐1,2‐dicarbonitrile (DDQ), resulted in the formation of pyrimido[5,4‐ c ]quinolines 206a – n (Scheme 28). [43] …”

Section: Synthesis and Reactivitymentioning

confidence: 99%

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Pyrimido[5,4‐c]quinolines: Synthesis from 3,4‐Di‐functionallized Quinoline, Reactivity and Biological Activities

Gouda,

Abu‐Hashem,

Ameen

et al. 2024

Chemistry & Biodiversity

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Quinoline and pyrimidine moieties are ubiquitous components in both natural and synthetic compounds, showcasing diverse applications. The fusion of these well‐known structures into hybrid molecules has garnered attention due to their intriguing biological properties. Particularly in the field of medicinal chemistry, numerous studies in the last decade have focused on pyrimido[5,4‐c]quinoline ring systems (PyQs5,4‐c). This review elucidates the synthesis of PyQs5,4‐c and their derivatives using 3,4‐difunctionalized quinoline as a key starting material. The preparation of PyQs5,4‐c involves a series of chemical transformations, including the Friedländer, Ullmann andBiginelli reaction, Vilsmeier‐Haack formylation, Suzuki coupling, and a one‐pot three‐component reaction. These synthetic routes not only offer access to diverse PyQs5,4‐c derivatives but also contribute to the expanding arsenal of methods in the synthesis of biologically relevant compounds.

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Section: From 4-haloquinolinementioning

confidence: 99%

“…Additionally, some ketones led to the formation of pyrimido [5,4-c]quinolines 211a,b under the same reaction conditions (Scheme 29). [43] Scheme 25. Synthesis of pyrimido [5,4-…”

Section: From 4-haloquinolinementioning

confidence: 99%

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Pyrimido[5,4‐c]quinolines: Synthesis from 3,4‐Di‐functionallized Quinoline, Reactivity and Biological Activities

Gouda,

Abu‐Hashem,

Ameen

et al. 2024

Chemistry & Biodiversity

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“…[1][2][3][4] In recent years, we have succeeded in establishing the convenient synthetic methods which enable us to access novel fluorine-containing dibenzo[b,h] [1,6]naphthyridines, thiochromeno [3,2-c]quinolines, and chromeno [3,2-c]quinolines via 4-dimethylamino-3-trifluoroacetylquinoline 1 as a synthetic intermediate. 5 We also reported novel synthesis of 1H-and 2H-pyrazolo [4,3-c]quinolines, 6 isoxazoloquinolines, 6 4-diazepino [6,5-c]quinolines, 6 pyrimido [5,4-c]quinolines, 7 and benzo[h] [1,6]naphthyridines 7 using the reaction of 1 with bifunctional nucleophiles. The key step on the above studies is a unique aromatic nucleophilic substitution of 4-dimethylamino moiety of trifluoroacetylated quinoline 1 with N-, S-, and O-nucleophiles (Scheme 1).…”

Section: Introductionmentioning

confidence: 99%

Computational Study for the Aromatic Nucleophilic Substitution of 4-Dimethylamino-3-trifluoroacetyl- quinoline with Various Nucleophiles

Okada¹,

Ota²,

Nakagawa³

et al. 2021

HETEROCYCLES

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The aromatic nucleophilic substitutions of 4-dimethylamino-3-trifluoroacetylquinoline 1 with amines, thiols, and alcohols are elucidated on the basis of DFT calculations. Our calculation results suggest that the reaction of 1 with amines giving N-N exchanged products 4 occurs via Meisenheimer type adducts V whereas the ones with thiols and alcohols proceed via the enol type adducts VII and IX to afford N-S and N-O exchanged products 8 and 9, respectively. It is also clarified that the conditions required for the successful substitution are not controlled by the activation energies on these processes, but by the energy changes on the processes from 1 to each intermediates, V, VII, and IX.

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ChemInform Abstract: Efficient Syntheses of Fluorine‐Containing Pyrimido[5,4‐c]quinolines and Benzo[h][1,6]naphthyridines by Condensation Reactions of 3‐Trifluoroacetylquinolin‐4‐amine with Aldehydes and Ketones.

et al. 2015

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Efficient Syntheses of Fluorine-Containing Pyrimido[5,4-c]quinolines and Benzo[h][1,6]naphthyridines by Condensation Reactions of 3-Trifluoroacetylquinolin-4-amine with Aldehydes andKetones. -3-Trifluoroacetyl-4-aminoquinoline (I) undergoes a three-component condensation reaction with aldehydes ammonia to afford pyrimidoquinoline derivatives as single or major products. Similar reaction of (I) with ketones gives benzonaphthyridine derivatives via a Friedlaender-type cyclization. -(OKADA*, E.; HATAKENAKA, M.; NAKANO, S.; SAKAEMURA, T.; MORI, T.; TERAUCHI, T.; Heterocycles 89 (2014) 10, 2303-2317, http://dx.

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Efficient Syntheses of Fluorine-Containing Pyrimido[5,4-c]quinolines and Benzo[h][1,6]naphthyridines by Condensation Reactions of 3-Trifluoro-acetylquinolin-4-amine with Aldehydes and Ketones

Cited by 4 publications

References 27 publications

Pyrimido[5,4‐c]quinolines: Synthesis from 3,4‐Di‐functionallized Quinoline, Reactivity and Biological Activities

Pyrimido[5,4‐c]quinolines: Synthesis from 3,4‐Di‐functionallized Quinoline, Reactivity and Biological Activities

Computational Study for the Aromatic Nucleophilic Substitution of 4-Dimethylamino-3-trifluoroacetyl- quinoline with Various Nucleophiles

ChemInform Abstract: Efficient Syntheses of Fluorine‐Containing Pyrimido[5,4‐c]quinolines and Benzo[h][1,6]naphthyridines by Condensation Reactions of 3‐Trifluoroacetylquinolin‐4‐amine with Aldehydes and Ketones.

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