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

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An Experimental and Theoretical Study of the 1,3-Dipolar Cyclo addition of Alloxan-Derived Azomethine Ylides to Cyclopropenes. / Filatov, Alexander S.; Selivanov, Stanislav I.; Shmakov, Stanislav V.; Larina, Anna G.; Boitsov, Vitali M.; Stepakov, Alexander V.

в: Synthesis (Germany), Том 54, № 7, ss-2021-g0625-op, 01.04.2022, стр. 1803-1816.

Результаты исследований: Научные публикации в периодических изданиях › статья › Рецензирование

Author

Filatov, Alexander S. ; Selivanov, Stanislav I. ; Shmakov, Stanislav V. ; Larina, Anna G. ; Boitsov, Vitali M. ; Stepakov, Alexander V. / An Experimental and Theoretical Study of the 1,3-Dipolar Cyclo addition of Alloxan-Derived Azomethine Ylides to Cyclopropenes. в: Synthesis (Germany). 2022 ; Том 54, № 7. стр. 1803-1816.

BibTeX

@article{3f588ebc1e204ac58373892ded30d73f,

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

abstract = "A diastereoselective synthesis of biologically interesting spirobarbiturates has been achieved via [3+2] cycloaddition of alloxanderived 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.",

keywords = "1,3-dipolar cycloaddition, alloxan, azomethine ylides, cyclopropenes, DFT calculations, diastereoselectivity, one-pot, three-component reactions, spirobarbiturates",

author = "Filatov, {Alexander S.} and Selivanov, {Stanislav I.} and Shmakov, {Stanislav V.} and Larina, {Anna G.} and Boitsov, {Vitali M.} and Stepakov, {Alexander V.}",

year = "2022",

month = apr,

day = "1",

doi = "10.1055/a-1700-3115",

language = "English",

volume = "54",

pages = "1803--1816",

journal = "Synthesis",

issn = "0039-7881",

publisher = "Georg Thieme Verlag",

number = "7",

}

RIS

TY - JOUR

T1 - An Experimental and Theoretical Study of the 1,3-Dipolar Cyclo addition of Alloxan-Derived Azomethine Ylides to Cyclopropenes

AU - Filatov, Alexander S.

AU - Selivanov, Stanislav I.

AU - Shmakov, Stanislav V.

AU - Larina, Anna G.

AU - Boitsov, Vitali M.

AU - Stepakov, Alexander V.

PY - 2022/4/1

Y1 - 2022/4/1

N2 - A diastereoselective synthesis of biologically interesting spirobarbiturates has been achieved via [3+2] cycloaddition of alloxanderived 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.

AB - A diastereoselective synthesis of biologically interesting spirobarbiturates has been achieved via [3+2] cycloaddition of alloxanderived 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.

KW - 1,3-dipolar cycloaddition

KW - alloxan

KW - azomethine ylides

KW - cyclopropenes

KW - DFT calculations

KW - diastereoselectivity

KW - one-pot, three-component reactions

KW - spirobarbiturates

UR - http://www.scopus.com/inward/record.url?scp=85122083970&partnerID=8YFLogxK

UR - https://www.mendeley.com/catalogue/0ef0f7b7-cdad-3c6f-b529-86dbd6eb8456/

U2 - 10.1055/a-1700-3115

DO - 10.1055/a-1700-3115

M3 - Article

AN - SCOPUS:85122083970

VL - 54

SP - 1803

EP - 1816

JO - Synthesis

JF - Synthesis

SN - 0039-7881

IS - 7

M1 - ss-2021-g0625-op

ER -

ID: 88142491