A short and efficient protocol for the synthesis of imidazo[1,5- a ]quinoxalin-4-ones from 3-aroylquinoxalinones and compounds with the aminomethylene moiety

Мамедов, В. А.; Калинин, А. А.; Zhukova, Nataliya; Syakaev, Victor V.; Ризванов, И. Х.; Latypov, Shamil K.; Sinyashin, Оleg G.

doi:10.1016/j.tet.2014.11.017

Cited by 6 publications

(2 citation statements)

References 28 publications

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“…Initially, it led to the formation of intermediate N‐(α‐quinoxalinylbenzylydene)benzylamine, which on further oxidative condensation, gave the final target compound [53] . The same group reported another method of development and utilized 3‐aroylquinoxalin‐2(1H)‐ones with α‐amino acids for the synthesis of target compounds [54] . Norris and team gave a regiospecific method for imidazo[1,5‐a]quinoxalin‐4(5H)‐one via intramolecular cyclization process of 34 [55] .…”

Section: Imidazo[15‐a]quinoxalinementioning

confidence: 99%

“…[53] The same group reported another method of development and utilized 3-aroylquinoxalin-2(1H)-ones with α-amino acids for the synthesis of target compounds. [54] Norris and team gave a regiospecific method for imidazo[1,5-a]quinoxalin-4(5H)-one via intramolecular cyclization process of 34. [55] Chen and his team caused reductive cyclization of 1-(o-nitrophenyl)imidazole-5carboxylate (35) to give target imidazoquinoxaline.…”

Section: Synthetic Strategiesmentioning

confidence: 99%

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Imidazoquinoxaline as a Privileged Fused Pharmacophore in Anticancer Drug Development: A Review of Synthetic Strategies and Medicinal Aspects

et al. 2022

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Cancer, the uncontrolled growth of cells, is not a single but a multifaceted disorder with malignant behavior, metastasis, and invasion, medically known as malignant neoplasm. The number of cases and morbidity due to cancer is rising alarmingly worldwide, causing around 21 % annually. Imidazoquinoxaline is a privileged scaffold with a wide range of pharmacological activities that is well explored for its anticancer potential. As a synthon, imidazoquinoxaline presents a large number of possibilities for structural modifications, which have attained the attention of many researchers for the development of new anticancer molecules with diverse improved target specificity and efficiency. Development of imiquimod followed by EAPB203 and EAPB503 derivatives further enhanced the popularity of this structural pharmacophore. In this report, we have focused on the anticancer potential of newly reported imidazoquinoxaline derivatives, along with their SAR studies and therapeutic potential. We have also enlisted the synthetic schemes reported for the synthesis of imidazoquinoxaline derivatives. The lead structural features described in this review will assist the researchers in designing and developing the novel imidazoquinoxaline pharmacophore containing anticancer compounds possessing the potential to interfere with various factors or mediators which are responsible for the progression of cancer. This report will also help in identifying the potent compounds which can be further evaluated in clinical trials for the development of new anticancer drugs with minimal to no side effects.

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Section: Imidazo[15‐a]quinoxalinementioning

confidence: 99%

Section: Synthetic Strategiesmentioning

confidence: 99%

Imidazoquinoxaline as a Privileged Fused Pharmacophore in Anticancer Drug Development: A Review of Synthetic Strategies and Medicinal Aspects

et al. 2022

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ChemInform Abstract: A Short and Efficient Protocol for the Synthesis of Imidazo[1,5‐a]quinoxalin‐4‐ones from 3‐Aroylquinoxalinones and Compounds with the Aminomethylene Moiety.

et al. 2015

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Sequential Decarboxylation, Substitution, Cyclization and Oxidation with Iodine‐DMSO Catalytic System: A New Methodology for the Construction of Imidazoquinoxaline Motifs

Chiranjeevi,

Kumar,

Rao

et al. 2024

ChemistrySelect

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A one‐pot synthetic protocol has been developed using aryl acetic acid as new and alternate surrogate for the synthesis of 4‐aryl imidazoquinoxalines with molecular iodine‐DMSO green catalytic system under classical heating at 100–110 °C. A variety of quinoxaline derivatives containing quinoline are prepared by using this methodology. This new protocol has a potential to tolerate broad substrates, that is, different amines and aryl acetic acids.

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A short and efficient protocol for the synthesis of imidazo[1,5- a ]quinoxalin-4-ones from 3-aroylquinoxalinones and compounds with the aminomethylene moiety

Cited by 6 publications

References 28 publications

Imidazoquinoxaline as a Privileged Fused Pharmacophore in Anticancer Drug Development: A Review of Synthetic Strategies and Medicinal Aspects

Imidazoquinoxaline as a Privileged Fused Pharmacophore in Anticancer Drug Development: A Review of Synthetic Strategies and Medicinal Aspects

ChemInform Abstract: A Short and Efficient Protocol for the Synthesis of Imidazo[1,5‐a]quinoxalin‐4‐ones from 3‐Aroylquinoxalinones and Compounds with the Aminomethylene Moiety.

Sequential Decarboxylation, Substitution, Cyclization and Oxidation with Iodine‐DMSO Catalytic System: A New Methodology for the Construction of Imidazoquinoxaline Motifs

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