A facile, metal-free, oxidative coupling of new 6-(hetero)aryl-[1,2,5]-oxadiazolo[3,4-b]pyrazines with pyrroles, indoles and carbazoles

Kvashnin, Yuriy A.; Kazin, Nikita A.; Verbitskiy, Egor V.; Svalova, Tatyana S.; Ivanova, Alla V.; Козицина, А. Н.; Слепухин, П. А.; Rusinov, Gennady L.; Чупахин, О. Н.; Charushin, Valery N.

doi:10.3998/ark.5550190.p009.828

Cited by 9 publications

(1 citation statement)

References 24 publications

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“…Verbitskiy and coworkers reported in 2016 a facile, transition metal free, one‐pot oxidative coupling reaction between 6‐(hetero)aryl‐[1,2,5]oxadiazolo[3,4‐b]pyrazines and pyrroles, indoles or carbazoles (Scheme 138). [155] …”

Section: C−h Functionalization Of Pyrrolesmentioning

confidence: 99%

Recent Advances in Functionalization of Pyrroles and their Translational Potential

Hunjan

Panday

Gupta

et al. 2021

The Chemical Record

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Among the known aromatic nitrogen heterocycles, pyrrole represents a privileged aromatic heterocycle ranging its occurrence in the key component of “pigments of life” to biologically active natural products to active pharmaceuticals. Pyrrole being an electron‐rich heteroaromatic compound, its predominant functionalization is legendary to aromatic electrophilic substitution reactions. Although a few excellent reviews on the functionalization of pyrroles including the reports by Baltazzi in 1963, Casiraghi and Rassu in 1995, and Banwell in 2006 are available, they are fragmentary and over fifteen years old, and do not cover the modern aspects of catalysis. A review covering a comprehensive package of direct functionalization on pyrroles via catalytic and non‐catalytic methods including their translational potential is described. Subsequent to statutory yet concise introduction, the classical functionalization on pyrroles using Lewis acids largely following an ionic mechanism is discussed. The subsequent discussion follows the various metal‐catalyzed C−H functionalization on pyrroles, which are otherwise difficult to implement by Lewis acids. A major emphasize is given on the radical based pyrrole functionalization under metal‐free oxidative conditions, which is otherwise poorly highlighted in the literature. Towards the end, the current development of pyrrole functionalization under photocatalyzed and electrochemical conditions is appended. Only a selected examples of substrates and important mechanisms are discussed for different methods highlighting their scopes and limitations. The aromatic nucleophillic substitution on pyrroles (being an electron‐rich heterocycle) happened to be the subject of recent investigations, which has also been covered accentuating their underlying conceptual development. Despite great achievements over the past several years in these areas, many challenges and problems are yet to be solved, which are all discussed in summary and outlook.

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Section: C−h Functionalization Of Pyrrolesmentioning

confidence: 99%

Recent Advances in Functionalization of Pyrroles and their Translational Potential

Hunjan

Panday

Gupta

et al. 2021

The Chemical Record

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9-Ethyl-3-{6-(het)aryl-[1,2,5]oxadiazolo[3,4-b]pyrazin-5-yl}-9H-carbazoles: synthesis and study of sensitivity to nitroaromatic compounds

et al. 2018

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Modification and application of 1,2,5-oxadiazolo[3,4-b]pyrazine derivatives: highlights and perspectives

et al. 2022

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A facile, metal-free, oxidative coupling of new 6-(hetero)aryl-[1,2,5]-oxadiazolo[3,4-b]pyrazines with pyrroles, indoles and carbazoles

Abstract: A facile, metal-free, oxidative coupling of new 6-(hetero)aryl-[1,2,5]-oxadiazolo [3,4-b]

Cited by 9 publications

References 24 publications

Recent Advances in Functionalization of Pyrroles and their Translational Potential

Recent Advances in Functionalization of Pyrroles and their Translational Potential

9-Ethyl-3-{6-(het)aryl-[1,2,5]oxadiazolo[3,4-b]pyrazin-5-yl}-9H-carbazoles: synthesis and study of sensitivity to nitroaromatic compounds

Modification and application of 1,2,5-oxadiazolo[3,4-b]pyrazine derivatives: highlights and perspectives

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