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Cyclization of 1-(4,4-diethoxybutyl)-3-aryl(thio)ureas to 2-arylpyrrolidines and 2,3´-bipyrrole derivatives

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Abstract

A reaction of 1-(4,4-diethoxybutyl)-3-phenylthiourea with resorcinol, 2-methylresorcinol, pyrogallol, and hydroquinone in chloroform in the presence of trifluoroacetic acid leads to 2-aryl-1-(N-phenylcarbamothioyl)pyrrolidines. 1-(4,4-Diethoxybutyl)-3-arylureas and 1-(4,4diethoxybutyl)-3-arylthioureas in the presence of an acid catalyst undergo intramolecular cyclization and dimerization with the formation of 1,1´-bis(N-arylcarbamo(thio)yl)-2,3´-bipyrrole derivatives.

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Authors and Affiliations

  1. A. E. Arbuzov Institute of Organic and Physical Chemistry, Kazan Scientific Center of the Russian Academy of Sciences, 8 ul. Akad. Arbuzova, 420088, Kazan, Russian Federation

    A. V. Smolobochkin, A. S. Gazizov, Yu. K. Voronina, A. R. Burilov & M. A. Pudovik

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  1. A. V. Smolobochkin
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  2. A. S. Gazizov
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  3. Yu. K. Voronina
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  4. A. R. Burilov
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  5. M. A. Pudovik
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Correspondence to A. S. Gazizov.

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Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, No. 3, pp. 0731—0734, March, 2016.

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Smolobochkin, A.V., Gazizov, A.S., Voronina, Y.K. et al. Cyclization of 1-(4,4-diethoxybutyl)-3-aryl(thio)ureas to 2-arylpyrrolidines and 2,3´-bipyrrole derivatives. Russ Chem Bull 65, 731–734 (2016). https://doi.org/10.1007/s11172-016-1364-5

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  • DOI: https://doi.org/10.1007/s11172-016-1364-5

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