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

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

doi:10.1007/s11172-016-1364-5

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

Authors: Smolobochkin A.V.¹, Gazizov A.S.¹, Voronina Y.K.¹, Burilov A.R.¹, Pudovik M.A.¹
Affiliations:
1. A. E. Arbuzov Institute of Organic and Physical Chemistry, Kazan Scientific Center of the Russian Academy of Sciences
Issue: Vol 65, No 3 (2016)
Pages: 731-734
Section: Full Articles
URL: https://journals.rcsi.science/1066-5285/article/view/237514
DOI: https://doi.org/10.1007/s11172-016-1364-5
ID: 237514

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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.