2-Hydroxy-3-alkylquinoxalines

L'Italien, Yvon J.; Banks, C. K.

doi:10.1021/ja01151a073

Cited by 24 publications

(6 citation statements)

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“…The structure of compound IIa was confirmed by elemental analysis and spectral methods, as well as by comparing with published data [6,7]. 3-Ethylquinoxalin-2(1H)-one (IIa) can readily be alkylated at the nitrogen atom with ethyl bromide under standard conditions [14] (in boiling dioxane in the presence of potassium hydroxide) to afford 1,3-diethylquinoxalin-2(1H)-one (IIb) (no O-alkyl derivative V is formed; Scheme 3).…”

Section: IVmentioning

confidence: 70%

“…The only reported method for the synthesis of 3-ethylquinoxalin-2(1H)-one (IIa) includes three steps: (1) reaction of ethyl α-(ethoxalyl)propionate [6] with o-phenylenediamine, (2) alkaline hydrolysis of intermediate ethyl α-(2-hydroxyquinoxalin-3yl)propionate, and (3) decarboxylation of the acid thus formed [7]. The procedure based on oxidation of 3-alkyltetrahydroquinoxalin-2-ones formed by condensation of o-phenylenediamine with α-halo carboxylic acids also seems to be unreasonable: the yield of the target 3-alkylquinoxalin-2(1H)-ones ranges from 8 to 34% [8].…”

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confidence: 99%

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Synthesis and Functionalization of 3-Ethylquinoxalin-2(1H)-one

et al. 2005

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A new and effective procedure was developed for the synthesis of 3-ethylquinoxalin-2(1H)-one from o-phenylenediamine and ethyl 2-oxobutanoate. The latter was prepared by the Grignard reaction of diethyl oxalate with ethylmagnesium bromide or iodide. The ethyl group in 3-ethylquinoxalin-2(1H)-one can readily be converted into various functional groups: α-bromoethyl, α-thiocyanato, α-azidoethyl, α-phenylaminoethyl, acetyl, and bromoacetyl. The reaction of 3-(bromoacetyl)quinoxalin-2(1H)-one with thiourea and hydrazine-1,2-dicarbothioamide gives the corresponding 3-(2-amino-4-thiazolyl) derivatives.We previously showed that 3-(α-chlorobenzyl)-quinoxalin-2(1H)-one (I), which is readily available via reaction of 3-chloro-3-phenyl-2-oxopropionates with o-phenylenediamine, is a convenient polyfunctional reagent for the synthesis of various fused quinoxaline derivatives, such as thiazolo[3,4-a]-, imidazo-[1,5-a]-, pyrrolo[1,2-a]-, pyrazolo[3,4-b]-, pyrano-[5,6-b]-, and indolizino[2,3-b]quinoxalines [1][2][3][4][5]. The key factor in the formation of all these compounds is favorable arrangement of the α-chlorobenzyl group with respect to the endocyclic imino and carbamoyl moieties. Replacement of the chlorine atom by appropriate groups gives rise to structural fragments necessary for the subsequent ring closure at the a or b side of the pyrazine ring in the initial quinoxaline.

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Section: IVmentioning

confidence: 70%

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confidence: 99%

Synthesis and Functionalization of 3-Ethylquinoxalin-2(1H)-one

et al. 2005

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“…Quinoxalinone intermediates 4a , 4b , 4c , 4d , 4e , 5 , and 6 ; corresponding amines 7a , 7b , 7c , 7d , and 7e ; and 5‐nitro‐benzotriazole 10 were prepared using previously reported procedures. All other chemicals used in this study were commercially available.…”

Section: Methodsmentioning

confidence: 99%

Synthesis of 2‐(Quinoxalin‐2‐ylamino‐benzotriazolyl) Pentanedioic Derivatives as Potential Anti‐Folate Agents

Briguglio

Piras

Corona

et al. 2015

Journal of Heterocyclic Chem

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Anti‐folate agents had a significant impact on therapeutic treatment plans for diseases such as cancer, and bacterial and parasitic infections, notably malaria. Quinoxaline derivatives showed in vitro anticancer activity and were able to inhibit both the dihydrofolate reductase and thymidylate synthase. Here, we decided to combine the chemical properties of quinoxalines and quinoxaline 1,4‐dioxides with those of benzotriazole nucleus with the aim to evaluate the resulting biological properties. Two main new series, including more than 60 compounds, were prepared. In the first one, the benzotriazole moiety was linked through the nitrogen atoms 1, 2, or 3, to a glutaric acid substituent to simulate a glutamic moiety. In the second series, the glutaric acid was substituted with acetic acid moiety to evaluate the effects of steric hindrance. Here, we describe the multistep chemical processes to obtain all titled quinoxalines starting from commercially available diamines. The classical oxidation of selected quinoxalines was unsuccessful, and we have come to an independent synthetic pathway to obtain new derivatives linked to the benzotriazole moieties starting from synthons bearing N‐oxide functionality.

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“…of methyl ester 6-Carboxy-3-methyl 99 -249.5 204-205,210 144-146 225 109-110 164-166,165-167 129-131 87 22,23,24,29, 126, 129, 130,131 88 135 69 22,129,152 9,147 22,24 24 9,147 24 [194][195][196]31,69,129,[196][197] 187,194.5-196,200 12,144,145 Ethyl ester 160-162 129 Ethyl ester 1-Phenyl deriv. of ethyl ester Methyl ester 1-Ally1 deriv.…”

Section: -Carboxymethylmentioning

confidence: 99%

Quinoxalin‐2‐Ones and Quinoxalme‐2,3‐Diones

1979

Chemistry of Heterocyclic Compounds: A Series of Monographs

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2-Hydroxy-3-alkylquinoxalines

Cited by 24 publications

References 0 publications

Synthesis and Functionalization of 3-Ethylquinoxalin-2(1H)-one

Synthesis and Functionalization of 3-Ethylquinoxalin-2(1H)-one

Synthesis of 2‐(Quinoxalin‐2‐ylamino‐benzotriazolyl) Pentanedioic Derivatives as Potential Anti‐Folate Agents

Quinoxalin‐2‐Ones and Quinoxalme‐2,3‐Diones

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