Studies on Quinoxaline N-Oxides. III

Hayashi, Eisaku; Iijima, Chihoko; Nagasawa, Yoko

doi:10.1248/yakushi1947.84.2_163

Cited by 13 publications

(4 citation statements)

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“…We tried to push reaction conditions raising the temperature up to 90°C to investigate the parameter relevance in the chemical behavior, and we observed, for compound 15e , not only the formation of dicarboxylic acid 21 (15–30% yield) but also the formation of its precursor, quinoxalinone 4e (50–60% yield). All of these confirm, as previously reported , that the increase of temperature over 60°C in this oxidative conditions on quinoxaline derivatives does not lead to N‐oxidation but rather to the oxidation at position 2 and eventually to hydrolysis of susceptible functions.…”

Section: Resultssupporting

confidence: 91%

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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Section: Resultssupporting

confidence: 91%

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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show abstract

“…Signals for 5-H were also shifted upfield compared with the corresponding signals in the parent heterocycle but an explanation for this is not so apparent. Chromatography on silica gel with benzene gave 6-metlzoxy- ( 10) Hydrolysis of either compounds (lo), in boiling ethanolic hydriodic acid, or (9), in boiling ethanolic hydrochloric acid, gave the lactam (11) (82 and 63%, respectively).…”

Section: E Mementioning

confidence: 99%

“…Treatment of the ketone (11) with methyl iodide by Heaney's method 'I gave the 6-niethoxy-derivative (80%), while treatment with acetic anhydride gave the 6-acetoxyderivative (88%).…”

Section: E Mementioning

confidence: 99%

“…The product contained (8) with its isomer (7). A similar procedure with the 6-acetoxy-derivative (6) gave the expected l-alkylated derivatives (9) and (11) together with the 6-methoxy-compound (10) , the last presumably formed by nucleoyhilic displacement of the acetoxy-group. No product corresponding to (7) was isolated. Both the 6-acetoxy-(9) and 6-methoxy-(10) derivatives could be converted into (11) and, in turn, (11) readily yielded (9) or (10).…”

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confidence: 91%

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