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Cyclization of 1-(4,4-diethoxybutyl)-3-arylureas: a case study

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Abstract

Reaction of nitrogen-containing acetals with aromatic compounds is a valuable method of synthesis of various heterocycles. Herein we report the study on the reaction of (4,4-diethoxybutyl)ureas with nucleophilic aromatics. We have found that the structure of the products mainly depends on the strength of the acid used as catalyst as well as aromatic nucleophile nature and its concentration. Either 2-arylpyrrolidines, diarylbutanes, bispyrrole derivatives, or pyrrolidinequinazolinones can be synthesized via variation of these factors. The proposed mechanism of the reaction is discussed.

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Acknowledgements

This work was supported by the Russian Science Foundation (Grant no. 14-50-00014).

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Authors and Affiliations

  1. A.E. Arbuzov Institute of Organic and Physical Chemistry, Kazan Scientific Center, Russian Academy of Sciences, Arbuzova Str., 8, Kazan, Russian Federation

    Andrey V. Smolobochkin, Almir S. Gazizov, Julia K. Voronina, Alexander R. Burilov & Michail A. Pudovik

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  1. Andrey V. Smolobochkin
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  2. Almir S. Gazizov
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  3. Julia K. Voronina
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  4. Alexander R. Burilov
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  5. Michail A. Pudovik
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Corresponding author

Correspondence to Almir S. Gazizov.

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Smolobochkin, A.V., Gazizov, A.S., Voronina, J.K. et al. Cyclization of 1-(4,4-diethoxybutyl)-3-arylureas: a case study. Monatsh Chem 149, 535–541 (2018). https://doi.org/10.1007/s00706-017-2080-z

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  • DOI: https://doi.org/10.1007/s00706-017-2080-z

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