Michail A. Pudovik

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

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

One-pot synthesis of novel s-triazine-containing polyphenols and imidazotriazinium salts

Study of the reaction of aminoacetal containing 1,3,5-triazine moiety with phenols is reported. Reaction conditions leading to the formation of either polyphenols modified with 1,3,5-triazine moiety or previously unknown 6-arylimidazo[1,2-a][1,3,5]triazin-5-ium salts with good yields are determined. Formation of triazinium salts proceeds via the dearylation of initially formed triazine-containing polyphenols.Graphical abstract.

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 and Structure of Aminophosphonates Containing 3,5-Di-Tert-Butyl-4-Hydroxyphenyl and Acetal Groups

GRAPHICAL ABSTRACT Abstract The reactions of dialkyl [(3,5-di-tert-butyl-4-oxo-2,5-cyclohexadienyl)methyl]phosphonates with N-nucleophiles (aminoacetaldehyde dimethyl acetal and diethyl [(2,2-dimethoxyethyl)aminomethyl]phosphonate give new aminophosphonates containing the 3,5-di-tert-butyl-4-hydroxyphenyl substituent, in addition to the acetal group. The crystal structure of diethyl {(3,5-di-tert-butyl-4-hydroxyphenyl)[(2,2-dimethoxyethyl)amino]methyl}phosphonate is elucidated. The presence of a chiral carbon atom and prochiral phosphorus atom in the aminophosphonate products is responsible for the complicated pattern in the 1H NMR spectra, the features of which are discussed.

Reactions of 2,4-diaryl 1,3,2,4-dithiadiphosphetane- 2,4-disulfides with resorcinol and 1,3-bis(2-hydroxyethoxy) benzene

Reactions of 2,4-diaryl 1,3,2,4-dithiadiphosphetane2,4-disulfides with resorcinol and 1,3-bis(2-hydroxyethoxy) benzene Ilyas S. Nizamova,b*, Yevgeniy N. Nikitinb, Lyubov A. Almetkinab, Gulnaz R. Sabirzyanovab, Alexander R. Burilova and Michail A. Pudovika aAE Arbuzov Institute of Organic and Physical Chemistry, 420088 Kazan, Arbuzov Street, 8, Russia; bKazan (Volga Region) Federal University, 420008 Kazan, Kremlyovskaya Street, 18, Russia

Synthesis of substituted ureas possessing alkyl aromatic fragments via the reaction of 1-(3,3-diethoxypropyl)ureas with phenols

Abstract In this article, we report the approach to the substituted ureas based on the reaction of 1-(3,3-diethoxypropyl)ureas with phenols. Depending on the nature of the phenol and urea the reaction leads either to diarylpropane and dibenzoxanthene derivatives or calixarenes. The proposed method benefits from mild reaction conditions, high product yields and operational simplicity. GRAPHICAL ABSTRACT

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

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.Graphical abstract

Synthesis of benzooxadiazocines via the acid-catalyzed reaction of pyrimidine-containing acetals with resorcinol derivatives

Herein, we report the synthesis of heteroannelated benzooxadiazocines via unusual reaction of pyrimidine-containing acetal with resorcinol derivatives.Graphical abstract