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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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.
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Language:English
Subjects:
Amides
Amino aldehydes
Biofilms
Cyclization
Nitrogen heterocycles
Reagents
Synthetic methods
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cited_by cdi_FETCH-LOGICAL-c3178-80c148ffdb65663c3a610f38502209664cbe56ac84cf82e50d3ae487ed9f5b3e3
cites cdi_FETCH-LOGICAL-c3178-80c148ffdb65663c3a610f38502209664cbe56ac84cf82e50d3ae487ed9f5b3e3
container_end_page 5719
container_issue 33
container_start_page 5709
container_title European journal of organic chemistry
container_volume 2019
creator 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.
description 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.
doi_str_mv 10.1002/ejoc.201900868
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subjects Amides
Amino aldehydes
Biofilms
Cyclization
Nitrogen heterocycles
Reagents
Synthetic methods
title Acid‐Catalyzed Intramolecular Imination / Nucleophilic Trapping of 4‐Aminobutanal Derivatives: One‐Pot Access to 2‐(Pyrazolyl)pyrrolidines
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