Reactions of polyhydric phenols with nitrogen-containing acetals in the synthesis of polyphenols and heterocyclic compounds

Газизов, А. С.; Burilov, A. R.; Пудовик, М. А.

doi:10.1007/s11172-016-1562-1

Cited by 3 publications

(2 citation statements)

References 31 publications

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“…Earlier, we developed a metal-free approach to 2-arylsubstitued pyrrolidine derivatives based on the acid-catalyzed intramolecular cyclization of N -(4,4-diethoxybutyl)ureas, leading to the formation of a pyrrolinium cation. Further Mannich-type reaction of this cyclic iminium ion with various electron-rich aromatic C -nucleophiles allowed us to obtain a range of 2-arylpyrrolidine-1-carboxamides [38,39,40,41,42,43,44,45]. The main benefits of this approach are the usage of easily accessible starting materials and its modularity, which allows wide variability in both the aromatic moiety and substituents at the nitrogen atom (Scheme 1).…”

Section: Introductionmentioning

confidence: 99%

Synthesis of Novel 2-(Het)arylpyrrolidine Derivatives and Evaluation of Their Anticancer and Anti-Biofilm Activity

et al. 2019

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A library of novel 2-(het)arylpyrrolidine-1-carboxamides were obtained via a modular approach based on the intramolecular cyclization/Mannich-type reaction of N-(4,4-diethoxybutyl)ureas. Their anti-cancer activities both in vitro and in vivo were tested. The in vitro activity of some compounds towards M-Hela tumor cell lines was twice that of the reference drug tamoxifen, whereas cytotoxicity towards normal Chang liver cell did not exceed the tamoxifen toxicity. In vivo studies showed that the number of surviving animals on day 60 of observation was up to 83% and increased life span (ILS) was up to 447%. Additionally, some pyrrolidine-1-carboxamides possessing a benzofuroxan moiety obtained were found to effectively suppress bacterial biofilm growth. Thus, these compounds are promising candidates for further development both as anti-cancer and anti-bacterial agents.

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Section: Introductionmentioning

confidence: 99%

Synthesis of Novel 2-(Het)arylpyrrolidine Derivatives and Evaluation of Their Anticancer and Anti-Biofilm Activity

et al. 2019

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“…Earlier, we have developed the metal‐free approach to the 2‐arylsubstitued pyrrolidine derivatives based on the acid‐catalyzed intramolecular imination of 4,4‐diethoxybutyl‐1‐amine derivatives leading to the formation of pyrrolinium cation. Further Mannich‐type reaction of this cyclic iminium ion with various electron‐rich aromatic nucleophiles allowed us to obtain a range of 2‐arylpyrrolidine derivatives …”

Section: Introductionmentioning

confidence: 99%

Acid‐Catalyzed Intramolecular Imination / Nucleophilic Trapping of 4‐Aminobutanal Derivatives: One‐Pot Access to 2‐(Pyrazolyl)pyrrolidines

et al. 2019

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A first successful synthesis of 2‐(pyrazolyl)pyrrolidines is reported starting from readily available reagents. A wide variety of N‐substituted 2‐(pyrazolyl)pyrrolidines are obtained with up to 96 % yield. The influence of the obtained compounds on biofilm formation by V. aquamarinus DSM 26054 and A. calcoaceticus VKPM B–10353 have been studied. Some of the tested compounds were found to suppress the growth of bacterial biofilms at nanomolar concentrations and thus are promising candidates for further studies.

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Iron‐Catalyzed Radical Cleavage/C−C Bond Formation of Acetal‐Derived Alkylsilyl Peroxides

Shiozaki

Sakurai

Sakamoto

et al. 2020

Chemistry An Asian Journal

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A novel radical‐based approach for the iron‐catalyzed selective cleavage of acetal‐derived alkylsilyl peroxides, followed by the formation of a carbon–carbon bond is reported. The reaction proceeds under mild reaction conditions and exhibits a broad substrate scope with respect to the acetal moiety and the carbon electrophile. Mechanistic studies suggest that the present reaction proceeds through a free‐radical process involving carbon radicals generated by the homolytic cleavage of a carbon–carbon bond within the acetal moiety. A synthetic application of this method to sugar‐derived alkylsilyl peroxides is also described.

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Reactions of polyhydric phenols with nitrogen-containing acetals in the synthesis of polyphenols and heterocyclic compounds

Cited by 3 publications

References 31 publications

Synthesis of Novel 2-(Het)arylpyrrolidine Derivatives and Evaluation of Their Anticancer and Anti-Biofilm Activity

Synthesis of Novel 2-(Het)arylpyrrolidine Derivatives and Evaluation of Their Anticancer and Anti-Biofilm Activity

Acid‐Catalyzed Intramolecular Imination / Nucleophilic Trapping of 4‐Aminobutanal Derivatives: One‐Pot Access to 2‐(Pyrazolyl)pyrrolidines

Iron‐Catalyzed Radical Cleavage/C−C Bond Formation of Acetal‐Derived Alkylsilyl Peroxides

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