Issue 4, 2021
From the journal:

New Journal of Chemistry

Imidazol-5-ones as a substrate for [1,5]-hydride shift triggered cyclization†

Elvira R. Zaitseva,ab   Alexander Yu. Smirnov, ORCID logo *a   Ivan N. Myasnyanko, ORCID logo a   Konstantin S. Mineev,a   Anatolii I. Sokolov,a   Tatyana N. Volkhina,bc   Andrey A. Mikhaylov, ORCID logo a   Nadezhda S. Baleevaa  and  Mikhail S. Baranovad  

* Corresponding authors

a Institute of Bioorganic Chemistry, Russian Academy of Sciences, Miklukho-Maklaya 16/10, Moscow, Russia
E-mail: alexmsu@yandex.ru

b D. Mendeleev University of Chemical Technology of Russia, 9 Miusskaya Sq., Moscow, Russia

c A.N. Nesmeyanov Institute of Organoelement Compounds, Russian Academy of Sciences, Vavilova Str., 28, Moscow, Russia

d Pirogov Russian National Research Medical University, Ostrovitianov 1, Moscow, Russia

Abstract

2-Dialkylamino-arylidene-imidazolones undergo intermolecular tandem [1,5]-hydride shift and cyclization to form spirocyclic tetrahydroquinoline derivatives under TiCl4 promotion. Different substitutions on each of the aryl, amino and imidazole fragments are tolerated, which results in 20+ examples and 25–95% yields.

Graphical abstract: Imidazol-5-ones as a substrate for [1,5]-hydride shift triggered cyclization

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Article information

DOI
https://doi.org/10.1039/D0NJ05738J
Article type
Communication
Submitted
24 Nov 2020
Accepted
07 Jan 2021
First published
07 Jan 2021

New J. Chem., 2021,45, 1805-1808

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Imidazol-5-ones as a substrate for [1,5]-hydride shift triggered cyclization

E. R. Zaitseva, A. Yu. Smirnov, I. N. Myasnyanko, K. S. Mineev, A. I. Sokolov, T. N. Volkhina, A. A. Mikhaylov, N. S. Baleeva and M. S. Baranov, New J. Chem., 2021, 45, 1805 DOI: 10.1039/D0NJ05738J

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