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

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]p...

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Published inSynthesis (Stuttgart) Vol. 54; no. 7; pp. 1803 - 1816
Main Authors Filatov, Alexander S., Selivanov, Stanislav I., Shmakov, Stanislav V., Larina, Anna G., Boitsov, Vitali M., Stepakov, Alexander V.
Format Journal Article
LanguageEnglish
Published STUTTGART Thieme Medical Publishers 01.04.2022
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
one-pot
DESIGN
cyclopropenes
ANNULATION
ANTICONVULSANT
REACTIVITY
spirobarbiturates
POTENTIAL 1,3-DIPOLES
SPIRO-ANALOGS
diastereoselectivity
DFT calculations
azomethine ylides
three-component reactions
alloxan
BARBITURIC-ACID
INHIBITORS
DERIVATIVES
1,3-dipolar cycloaddition
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Summary: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.
ISSN:0039-7881
1437-210X
DOI:10.1055/a-1700-3115