Nucleophilic Cyclization/Electrophilic Substitution of (2,2-Dialkoxyethyl)ureas: Highly Regioselective Access to Novel 4-(Het)arylimidazolidinones and Benzo[d][1,3]diazepinones

Andrey V. Smolobochkin; Almir S. Gazizov; Nazerke K. Otegen; Julia K. Voronina; Anna G. Strelnik; Aida I. Samigullina; Alexander R. Burilov; Michail A. Pudovik

doi:10.1055/s-0040-1707864

Synthesis, Table of Contents

Synthesis 2020; 52(21): 3263-3271
DOI: 10.1055/s-0040-1707864

special topic

Nucleophilic Cyclization/Electrophilic Substitution of (2,2-Dialkoxyethyl)ureas: Highly Regioselective Access to Novel 4-(Het)arylimidazolidinones and Benzo[d][1,3]diazepinones

Andrey V. Smolobochkin ∗

^aArbuzov Institute of Organic and Physical Chemistry, FRC Kazan Scientific Center, Russian Academy of Sciences, 420088, Arbuzova str., 8, Kazan, Russian Federation Email: smolobochkin@iopc.ru

,

Almir S. Gazizov ∗

^aArbuzov Institute of Organic and Physical Chemistry, FRC Kazan Scientific Center, Russian Academy of Sciences, 420088, Arbuzova str., 8, Kazan, Russian Federation Email: smolobochkin@iopc.ru

,

Nazerke K. Otegen

^bKazan National Research Technological University, Karl Marx str., 68, 420015 Kazan, Russian Federation

,

Julia K. Voronina

^cN.S. Kurnakov Institute of General and Inorganic Chemistry, Russian Academy of Sciences, Leninsky Ave., 31, 119991 Moscow, Russian Federation

^dG.V. Plekhanov Russian University of Economics, Stremyanny Per., 36, 117997 Moscow, Russian Federation

,

Anna G. Strelnik

^aArbuzov Institute of Organic and Physical Chemistry, FRC Kazan Scientific Center, Russian Academy of Sciences, 420088, Arbuzova str., 8, Kazan, Russian Federation Email: smolobochkin@iopc.ru

,

Aida I. Samigullina

^aArbuzov Institute of Organic and Physical Chemistry, FRC Kazan Scientific Center, Russian Academy of Sciences, 420088, Arbuzova str., 8, Kazan, Russian Federation Email: smolobochkin@iopc.ru

,

Alexander R. Burilov

^aArbuzov Institute of Organic and Physical Chemistry, FRC Kazan Scientific Center, Russian Academy of Sciences, 420088, Arbuzova str., 8, Kazan, Russian Federation Email: smolobochkin@iopc.ru

,

Michail A. Pudovik

^aArbuzov Institute of Organic and Physical Chemistry, FRC Kazan Scientific Center, Russian Academy of Sciences, 420088, Arbuzova str., 8, Kazan, Russian Federation Email: smolobochkin@iopc.ru

› Author Affiliations

Abstract

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Published as part of the Special Topic Recent Advances in Amide Bond Formation

Abstract

Imidazolidin-2-one and 1,3-benzodiazepin-2-one scaffolds are structural motifs of many biologically active compounds. Herein, we report a highly regioselective acid-catalyzed intramolecular nucleophilic cyclization/intermolecular electrophilic substitution reaction sequence of (2,2-dialkoxyethyl)ureas. The reaction benefits from readily available starting materials, a simple workup procedure, moderate to high yields of target compounds, and provides a convenient entry to previously unknown 4-(het)arylimidazolidinones and 5-(het)arylbenzodiazepinones. The proposed mechanism of the reaction is also discussed.

Key words

(2,2-dialkoxyethyl)ureas - imidazolidin-2-ones - 1,3-benzodiazepin-2-ones - cyclization - cyclic ureas

Full Text

References

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