Synthesis
DOI: 10.1055/a-1700-3115
paper

An Experimental and Theoretical Study of the 1,3-Dipolar Cyclo­addition of Alloxan-Derived Azomethine Ylides to Cyclopropenes

Alexander S. Filatov
a  Saint-Petersburg State University, Universitetskaya nab. 7/9, 199034, St. Petersburg, Russian Federation
,
Stanislav I. Selivanov
a  Saint-Petersburg State University, Universitetskaya nab. 7/9, 199034, St. Petersburg, Russian Federation
,
Stanislav V. Shmakov
b  Saint Petersburg National Research Academic University of the Russian Academy of Sciences, ul. Khlopina 8/3, 194021, St. Petersburg, Russian Federation
,
Anna G. Larina
a  Saint-Petersburg State University, Universitetskaya nab. 7/9, 199034, St. Petersburg, Russian Federation
,
Vitali M. Boitsov
b  Saint Petersburg National Research Academic University of the Russian Academy of Sciences, ul. Khlopina 8/3, 194021, St. Petersburg, Russian Federation
,
Alexander V. Stepakov
a  Saint-Petersburg State University, Universitetskaya nab. 7/9, 199034, St. Petersburg, Russian Federation
c  Saint-Petersburg State Institute of Technology, Moskovskii pr. 26, 190013, St. Petersburg, Russian Federation
› Author Affiliations
The authors are grateful for the financial support from the Russian Science Foundation (RSF 20-15-00332).


Abstract

A diastereoselective synthesis of biologically interesting spirobarbiturates has been achieved via [3+2] cycloaddition of alloxan-derived azomethine ylides to 3-R-1,2-diphenylcyclopropenes. With this approach, a range of spirobarbiturate-3-azabicyclo[3.1.0]hexanes and spirobarbiturate-cyclopropa[a]pyrrolizines were obtained in moderate to good yields with excellent diastereoselectivities. DFT calculations (M11 density functional theory) were carried out to shed light on the molecular mechanism of 1,3-dipolar cycloaddition of alloxan-derived azomethine ylides to cyclopropenes. The cytotoxic activity of some obtained compounds against human erythroleukemia (K562) cell line was evaluated in vitro by MTS-assay.

Supporting Information



Publication History

Received: 15 October 2021

Accepted after revision: 17 November 2021

Publication Date:
17 November 2021 (online)

© 2021. Thieme. All rights reserved

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