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

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...

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Bibliographic Details
Published in:European journal of organic chemistry 2019-09, Vol.2019 (33), p.5709-5719
Main Authors: Smolobochkin, Andrey V., Rizbayeva, Tanzilya S., Gazizov, Almir S., Voronina, Julia K., Dobrynin, Alexey B., Gildebrant, Anastasiya V., Strelnik, Anna G., Sazykin, Ivan S., Burilov, Alexander R., Pudovik, Michail A., Sazykina, Marina A.
Format: Article
Language:English
Subjects:
Amides
Amino aldehydes
Biofilms
Cyclization
Nitrogen heterocycles
Reagents
Synthetic methods
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Summary: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. A first successful synthesis of 2‐(pyrazolyl)pyrrolidines via a metal‐free approach is reported. The proposed approach relies on intramolecular imination / nucleophilic trapping of 4‐aminobutanal acetals with pyrazolones and provides easy entry to the previously unknown class of 2‐(hetaryl) substituted pyrrolidines.
ISSN:1434-193X
1099-0690
DOI:10.1002/ejoc.201900868