3,4-Dihydroquinoxalin-2-ones: recent advances in synthesis and bioactivities (microreview)

Kristoffersen, Tone; Hansen, Jørn H.

doi:10.1007/s10593-017-2052-6

Cited by 9 publications

(6 citation statements)

References 18 publications

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“…Acetone, cyclopentanone, cyclohexanone and octan-2-one react successfully. Similar results were obtained using trichloromethylcarbinol under mild PTC, allowing a high degree of tolerance towards the substituents R 1 and R 2 [ 54 , 55 ].…”

Section: Applications Of Bargellini Reactionssupporting

confidence: 70%

The 115 Years Old Multicomponent Bargellini Reaction: Perspectives and New Applications

et al. 2021

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Despite its uniqueness, the Bargellini multicomponent reaction remains barely known by the most part of chemists. This can be ascribed to the fact that this transformation has not been adequately reviewed in the classic books of named reactions in organic chemistry. Nevertheless, several works on this reaction have been carried out over the years, many of them were written in Italian in the period 1929–1966. In this review article we extensively cover, in a chronological order, the most important applications of the Bargellini reaction reported to date, with the hope that this knowledge-sharing will help chemists to properly use this multicomponent transformation and imagine novel reactivities based on it.

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Section: Applications Of Bargellini Reactionssupporting

confidence: 70%

The 115 Years Old Multicomponent Bargellini Reaction: Perspectives and New Applications

et al. 2021

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“…[3] Ther emarkable examples reported by the groups of Hayashi, [4a] Zhu, [4b] Aggarwal, [4c] Pai¼o, [4d] Zhang, [4e] Masson, [4f] Dixon [4g] showed additional key-features of this tool, in securing wide molecular diversity and rapid access to libraries of compounds necessary for bioassay and drug discovery,thus resulting particularly appealing from an industrial perspective. [4] Chiral dihydroquinoxalinones are recognized as privileged pharmacophores of broad interest in medicinal chemistry,f ound in av ariety of bioactive compounds and pharmaceuticals [5] displaying anti-HIV, [6] antineoplastic, [7] anti-inflammatory [8] activities,f ungicidal properties [9] and used in the control of cardiovascular disease. [10] Moreover,t hey can serve as precursors of enantioenriched tetrahydroquinoxalines,w hich are another class of heterocycles endowed with several biological activities.…”

Section: Introductionmentioning

confidence: 99%

Catalytic Enantioselective Access to Dihydroquinoxalinones via Formal α‐Halo Acyl Halide Synthon in One Pot

et al. 2021

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An enantioselective one‐pot catalytic strategy to dihydroquinoxalinones, featuring novel 1‐phenylsulfonyl‐1‐cyano enantioenriched epoxides as masked α‐halo acyl halide synthons, followed by a domino ring‐opening cyclization (DROC), is documented. A popular quinine‐derived urea served as the catalyst in two out of the three steps performed in the same solvent using commercially available aldehydes, (phenylsulfonyl)acetonitrile, cumyl hydroperoxide and 1,2‐phenylendiamines. Medicinally relevant 3‐aryl/alkyl‐substituted heterocycles are isolated in generally good to high overall yield and high enantioselectivity (up to 99 % ee). A rare example of excellent reusability of an organocatalyst at higher scale, subjected to oxidative conditions, is demonstrated. Mechanistically, labile α‐ketosulfone has been detected as the intermediate involved in the DROC process. Theoretical calculations on the key epoxidation step rationalize the observed stereocontrol, highlighting the important role played by the sulfone group.

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“…We have recently sought novel synthetic approaches to quinoxalines and dihydroquinoxalinones for synthetic and biological applications. [ 5,6 ] Several methods exist for generating dihydroquinoxalinones starting from α‐amino acids, [ 6b ] α‐haloesters, α,β‐unsaturated esters [ 6e ] and α‐diazoesters (Scheme 1). These are typically characterized by long reaction times and/or use of metal catalysts such as copper or rhodium.…”

Section: Introductionmentioning

confidence: 99%

“…The shortest reaction time was reported by Kamila and Biehl using microwave irradiation with α‐bromoesters and phenylenediamines in the presence of DBU (6 minutes), however, the transformation had extremely limited scope as presented. [ 6d ] There are other notable metal‐free approaches to these heterocycles employing hypervalent iodine reagents and boron‐catalysis, however, prolonged reaction times are typically required. [ 6j,6k ] Overall, the development of more rapid, simple, clean and practical reaction conditions is still an important synthetic goal for generating these heterocycles.…”

Section: Introductionmentioning

confidence: 99%

“…[ 6d ] There are other notable metal‐free approaches to these heterocycles employing hypervalent iodine reagents and boron‐catalysis, however, prolonged reaction times are typically required. [ 6j,6k ] Overall, the development of more rapid, simple, clean and practical reaction conditions is still an important synthetic goal for generating these heterocycles.…”

Section: Introductionmentioning

confidence: 99%

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Microwave‐Assisted Synthesis of Heterocycles from Aryldiazoacetates**

et al. 2020

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Herein, we describe a rapid microwave‐assisted, metal‐free synthesis of substituted quinoxalinones and quinoxalines using the carbene‐mediated reaction between aryldiazo esters and 1,2‐diamines. The reaction can encompass a range of substituents and structural variations to afford quinoxalin‐2‐ones in 14–80 % yield and corresponding quinoxalines in good to excellent yields upon oxidation (67–96 %). The approach can be employed to generate symmetrical and unsymmetrical 2,3‐diarylquinoxalines, bis‐quinoxalines as well as novel quinoxaline‐substituted diazo esters and should be a valuable addition to the heterocycle synthesis toolbox.

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3,4-Dihydroquinoxalin-2-ones: recent advances in synthesis and bioactivities (microreview)

Cited by 9 publications

References 18 publications

The 115 Years Old Multicomponent Bargellini Reaction: Perspectives and New Applications

The 115 Years Old Multicomponent Bargellini Reaction: Perspectives and New Applications

Catalytic Enantioselective Access to Dihydroquinoxalinones via Formal α‐Halo Acyl Halide Synthon in One Pot

Microwave‐Assisted Synthesis of Heterocycles from Aryldiazoacetates**

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