A. V. Smolobochkin

Interaction of 2-Naphthol with γ-Ureidoacetals. A New Method for the Synthesis of 2-Arylpyrrolidines

We report a new, single-stage method for the synthesis of 2-arylpyrrolidines, based on an acid-catalyzed reaction of 2-naphthol with γ-ureidoacetals, enabling the preparation of the target compounds under mild conditions, while avoiding costly reagents and catalysts.

Acid-Catalyzed Reaction of (4,4-Diethoxybutyl)ureas with Phenols as a Novel Approach to the Synthesis of α-Arylpyrrolidines

Abstract 1-(4,4-Diethoxybutyl)-3-alkylureas undergo intramolecular cyclization in the presence of trifluoroacetic acid and various phenols, leading to the new N-alkyl-2-arylpyrrolidine-1-carboxamides with moderate to excellent yields. It was found that these compounds undergo spontaneous solid-phase epimerization at room temperature. Advantages of the proposed approach are mild reaction conditions and no need for expensive reagents or catalysts. GRAPHICAL ABSTRACT

Synthesis of novel 2-arylpyrrolidines by the reaction of 1-(4,4-diethoxybutyl)urea with resorcinols

Reaction of 1-(4,4-diethoxybutyl)urea with resorcinol, 2-methylresorcinol and pyrogallol in chloroform in the presence of trifluoroacetic acid affords new 2,2′-(1,3-phenylene)-bis(pyrrolidine-1-carboxamides).

Facile synthesis of 2-(2-arylpyrrolidin-1-yl)pyrimidines via acid-catalyzed reaction of N-(4,4-diethoxybutyl)pyrimidin-2-amine with phenols

N-(4,4-diethoxybutyl)pyrimidin-2-amine undergoes acid-catalyzed intramolecular cyclisation in the presence of phenols leading to the formation of 2-(2-arylpyrrolidin-1-yl)pyrimidine derivatives. Target compounds were obtained with moderate to good yields by operationally simple one-step procedure.Graphical abstract

Reaction of N-cyclohexyl-2-(2-hydroxynaphthalen-1-yl)pyrrolidine-1-carboxamide with resorcinol and its derivatives and synthesis of polyphenols

An acid-catalyzed pyrrolidine ring opening in 2-(2-hydroxynaphthalen-1-yl)pyrrolidine-1-carboxamides in the presence of resorcinols furnished new calix[4]resorcinols or 1,1-diarylbutanes modified with urea fragments. The process follows the retro-Mannich reaction mechanism, with the 2-naphthol fragment playing the role of the leaving group.

Reaction of 1-aryl-3-(4,4-diethoxybutyl)ureas with phenols. Synthesis of 2-arylpyrrolidines

Acid-catalyzed reaction of phenols with 1-(4,4-diethoxybutyl)urea derivatives gave new 2-arylpyrrolidines containing 4-bromoresorcinol and hydroquinone fragments. The described reaction is advantageous due to its mild conditions and no necessity of using expensive or toxic catalyst.

Acid-catalyzed intramolecular cyclization of N-(4,4-diethoxybutyl)sulfonamides as a novel approach to the 1-sulfonyl-2-arylpyrrolidines

ABSTRACT Herein we report our studies on the acid-catalyzed cyclisation of N-(4,4-diethoxybutyl)sulfonamides at the presence of polyatomic phenols as an efficient one-pot approach to the synthesis of 1-sulfonyl-2-arylpyrrolidines from the acyclic precursors. GRAPHICAL ABSTRACT

Synthesis of 2-arylpyrrolidine-1-carboxamides via acid-catalyzed reaction of (4,4-diethoxybutyl)ureas with 3-aminophenol

Herein we report the synthesis of previously unknown 2-arylpyrrolidine-1-carboxamides containing aminophenol moiety via a novel approach developed by us, namely, acid-catalyzed cyclization of (4,4-diethoxybutyl)ureas in the presence of 3-aminophenol. The proposed approach benefits from mild reaction conditions, use of inexpensive and common solvents and catalyst, and allows to obtain target compounds with good to high yields.Graphical abstract

Synthesis of 1-(arenesulfonyl)-2-arylpyrrolidines by reaction of N-(4,4-diethoxybutyl)-4-methylbenzene-sulfonamide with phenols

New 1-(arenesulfonyl)-2-arylpyrrolidines were synthesized by reactions of several phenols with N-(4,4-diethoxybutyl)-4-methylbenzenesulfonamide in the presence of trifluoroacetic acid.

Nitrogen-containing acetals and ketals in the synthesis of pyrrolidine derivatives

This review offers analysis and generalization of data regarding the synthesis of substituted pyrrolidines by using nitrogen-containing acetals and ketals as starting compounds published from year 2000 to 2016. Particular attention has been focused on the synthesis of pyrrolidines that are substituted at position 2. Biological activity data for several pyrrolidine derivatives are reported.