Convenient synthesis of 2-(het)arylpyrrolidines via stable 1-pyrrolinium salts

Melyashova, A. S.; Smolobochkin, Аndrey V.; Газизов, А. С.; Voronina, Julia K.; Бурилов, А. Р.; Пудовик, М. А.

doi:10.1016/j.tet.2019.130681

Cited by 8 publications

(2 citation statements)

References 18 publications

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“…Previously, we have utilized 1-pyrrolinium cations, either pre-formed 41 or generated in situ from N- (4,4diethoxybutyl)sulfonylamides or N- (4,4-diethoxybutyl)ureas, 42,43 for the synthesis of various 2-(het)arylpyrrolidine derivatives using electron-rich aromatics and heterocycles as C-nucleophiles. In general, this chemistry is similar to cyclic iminium ion chemistry developed by Speckamp and coworkers except that silyl enol ethers, 44 allylsilanes, 45 or alkenes 46,47 were used as C-nucleophiles in this case.…”

Section: Published As Part Of the Special Topic Recent Advances In Ammentioning

confidence: 99%

Nucleophilic Cyclization/Electrophilic Substitution of (2,2-Dialkoxyethyl)ureas: Highly Regioselective Access to Novel 4-(Het)arylimidazolidinones and Benzo[d][1,3]diazepinones

et al. 2020

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Imidazolidin-2-one and 1,3-benzodiazepin-2-one scaffolds are structural motifs of many biologically active compounds. Herein, we report a highly regioselective acid-catalyzed intramolecular nucleophilic cyclization/intermolecular electrophilic substitution reaction sequence of (2,2-dialkoxyethyl)ureas. The reaction benefits from readily available starting materials, a simple workup procedure, moderate to high yields of target compounds, and provides a convenient entry to previously unknown 4-(het)arylimidazolidinones and 5-(het)arylbenzodiazepinones. The proposed mechanism of the reaction is also discussed.

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Section: Published As Part Of the Special Topic Recent Advances In Ammentioning

confidence: 99%

Nucleophilic Cyclization/Electrophilic Substitution of (2,2-Dialkoxyethyl)ureas: Highly Regioselective Access to Novel 4-(Het)arylimidazolidinones and Benzo[d][1,3]diazepinones

et al. 2020

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“…These data and our deep interest in the chemistry of 1-pyrrolines , led us to investigate the behavior of N -nucleophiles in this reaction. As a result of our research, herein, we report the synthesis of pyrazolo[3,4- b ]pyridines via the reaction of 3-arylidene-1-pyrrolines with aminopyrazole derivatives.…”

Section: Introductionmentioning

confidence: 99%

One-Step Synthesis of Functionalized Pyrazolo[3,4-b]pyridines via Ring Opening of the Pyrrolinium Ion

et al. 2023

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Herein, we report a highly regioselective one-pot synthesis of pyrazolo [3,4-b]pyridines via the reaction of 3-arylidene-1-pyrrolines with aminopyrazoles. The reaction proceeds through the sequential nucleophilic addition/electrophilic substitution/C−N bond cleavage and provides easy access to pyrazolo[3,4-b]pyridine derivatives featuring a primary amino group. Moreover, the reaction can be terminated at the electrophilic substitution stage, thus providing convenient entry to the hardly accessible pyrazolopyrrolopyridine scaffold.

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Synthesis of Novel 2-Hetarylpyrrolidines via the Reaction of N-(4,4-diethoxybutyl)amidophosphates with C-nucleophiles

Smolobochkin

Турманов

Газизов

et al. 2020

Chem Heterocycl Comp

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Convenient synthesis of 2-(het)arylpyrrolidines via stable 1-pyrrolinium salts

Cited by 8 publications

References 18 publications

Nucleophilic Cyclization/Electrophilic Substitution of (2,2-Dialkoxyethyl)ureas: Highly Regioselective Access to Novel 4-(Het)arylimidazolidinones and Benzo[d][1,3]diazepinones

Nucleophilic Cyclization/Electrophilic Substitution of (2,2-Dialkoxyethyl)ureas: Highly Regioselective Access to Novel 4-(Het)arylimidazolidinones and Benzo[d][1,3]diazepinones

One-Step Synthesis of Functionalized Pyrazolo[3,4-b]pyridines via Ring Opening of the Pyrrolinium Ion

Synthesis of Novel 2-Hetarylpyrrolidines via the Reaction of N-(4,4-diethoxybutyl)amidophosphates with C-nucleophiles

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