Acetylene based short route from 2,2,6,6-tetramethylpiperidin-4-one oxime to 2-(pyrazol-5-yl)-4,5,6,7-tetrahydropyrrolo[3,2-c]pyridines

Sagitova, Elena F.; Tomilin, Denis N.; Петрова, О. В.; Budaev, Arsalan B.; Собенина, Л. Н.; Трофимов, Б. А.; Yang, Guoqiang; Hu, Rui

doi:10.1016/j.mencom.2019.11.018

Mendeleev Communications

2019

DOI: 10.1016/j.mencom.2019.11.018

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Acetylene based short route from 2,2,6,6-tetramethylpiperidin-4-one oxime to 2-(pyrazol-5-yl)-4,5,6,7-tetrahydropyrrolo[3,2-c]pyridines

Elena F. Sagitova

Denis N. Tomilin

О. В. Петрова

et al.

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Cited by 2 publications

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“…The formation of tetrahydroindolyl dihydrodiazepine 68b.5.4. Cyclization with Hydrazine: Synthesis of Pyrrolyl PyrazolesThe building up of the pyrazole ring over acetylenic moiety of pyrrolopyridine propynones 21 via its ring closure with hydrazine gave 4,5,6,7-tetrahydropyrrolo[3,2-c]pyridine-pyrazole ensembles 69 in 92-98% yields (Scheme 38)[59].…”

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Recent Strides in the Transition Metal-Free Cross-Coupling of Haloacetylenes with Electron-Rich Heterocycles in Solid Media

Собенина

Трофимов

2020

Molecules

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The publications covering new, transition metal-free cross-coupling reactions of pyrroles with electrophilic haloacetylenes in solid medium of metal oxides and salts to regioselectively afford 2-ethynylpyrroles are discussed. The reactions proceed at room temperature without catalyst and base under solvent-free conditions. These ethynylation reactions seem to be particularly important, since the common Sonogashira coupling does not allow ethynylpyrroles with strong electron-withdrawing substituents at the acetylenic fragments to be synthesized. The results on the behavior of furans, thiophenes, and pyrazoles under the conditions of these reactions are also provided. The reactivity and structural peculiarities of nucleophilic addition to the activated acetylene moiety of the novel C-ethynylpyrroles are considered.

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confidence: 99%

Recent Strides in the Transition Metal-Free Cross-Coupling of Haloacetylenes with Electron-Rich Heterocycles in Solid Media

Собенина

Трофимов

2020

Molecules

Self Cite

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A convenient one-pot two-step synthesis of pyrazolylphosphonates from ethynylphosphonate

Mitrofanov

Beletskaya

2021

Mendeleev Communications

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Acetylene based short route from 2,2,6,6-tetramethylpiperidin-4-one oxime to 2-(pyrazol-5-yl)-4,5,6,7-tetrahydropyrrolo[3,2-c]pyridines

Cited by 2 publications

References 31 publications

Recent Strides in the Transition Metal-Free Cross-Coupling of Haloacetylenes with Electron-Rich Heterocycles in Solid Media

Recent Strides in the Transition Metal-Free Cross-Coupling of Haloacetylenes with Electron-Rich Heterocycles in Solid Media

A convenient one-pot two-step synthesis of pyrazolylphosphonates from ethynylphosphonate

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