Standard

Oxidative addition of N-aminophthalimide to 3,4-dihydro-2H-thiopyrans, their S-oxides, and S,S-dioxides. / Меркулова, Екатерина; Spiridonova, Dar'ya V.; Колобов, Алексей Владиславович; Kuznetsov, Mikhail A.; Pankova, Alena S.

в: Tetrahedron Letters, Том 94, 153715, 30.03.2022.

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

Harvard

Меркулова, Е, Spiridonova, DV, Колобов, АВ, Kuznetsov, MA & Pankova, AS 2022, 'Oxidative addition of N-aminophthalimide to 3,4-dihydro-2H-thiopyrans, their S-oxides, and S,S-dioxides', Tetrahedron Letters, Том. 94, 153715. https://doi.org/10.1016/j.tetlet.2022.153715

APA

Меркулова, Е., Spiridonova, D. V., Колобов, А. В., Kuznetsov, M. A., & Pankova, A. S. (2022). Oxidative addition of N-aminophthalimide to 3,4-dihydro-2H-thiopyrans, their S-oxides, and S,S-dioxides. Tetrahedron Letters, 94, [153715]. https://doi.org/10.1016/j.tetlet.2022.153715

Vancouver

Меркулова Е, Spiridonova DV, Колобов АВ, Kuznetsov MA, Pankova AS. Oxidative addition of N-aminophthalimide to 3,4-dihydro-2H-thiopyrans, their S-oxides, and S,S-dioxides. Tetrahedron Letters. 2022 Март 30;94. 153715. https://doi.org/10.1016/j.tetlet.2022.153715

Author

Меркулова, Екатерина ; Spiridonova, Dar'ya V. ; Колобов, Алексей Владиславович ; Kuznetsov, Mikhail A. ; Pankova, Alena S. / Oxidative addition of N-aminophthalimide to 3,4-dihydro-2H-thiopyrans, their S-oxides, and S,S-dioxides. в: Tetrahedron Letters. 2022 ; Том 94.

BibTeX

@article{a77e3fd553144c03a03e1027eed351f8,
title = "Oxidative addition of N-aminophthalimide to 3,4-dihydro-2H-thiopyrans, their S-oxides, and S,S-dioxides",
abstract = "Selectivity of nitrene addition to the C[dbnd]C[sbnd]S[sbnd] fragment depends on the oxidative state of the sulfur atom as has been exemplified on various derivatives of 3,4-dihydro-2H-thiopyran under conditions of oxidative aminoaziridination. A unique structure with 2-thia-7-azabicyclo[4.1.0]heptane-2,2-dioxide core was obtained via addition of nitrene to the C[dbnd]C bond of thiopyran S,S-dioxide. For an unoxidized thiopyran, only en(phthaloyl)hydrazine resulted after cleavage of the initially formed aziridine. S-Oxide trapped the nitrene by the sulfur atom to form the sulfoximine leaving the double bond unaffected.",
keywords = "Aziridine, N-Aminophthalimide, Nitrene, Sulfone, Sulfoximine, Thiopyran",
author = "Екатерина Меркулова and Spiridonova, {Dar'ya V.} and Колобов, {Алексей Владиславович} and Kuznetsov, {Mikhail A.} and Pankova, {Alena S.}",
note = "Publisher Copyright: {\textcopyright} 2022 Elsevier Ltd",
year = "2022",
month = mar,
day = "30",
doi = "10.1016/j.tetlet.2022.153715",
language = "English",
volume = "94",
journal = "Tetrahedron Letters",
issn = "0040-4039",
publisher = "Elsevier",

}

RIS

TY - JOUR

T1 - Oxidative addition of N-aminophthalimide to 3,4-dihydro-2H-thiopyrans, their S-oxides, and S,S-dioxides

AU - Меркулова, Екатерина

AU - Spiridonova, Dar'ya V.

AU - Колобов, Алексей Владиславович

AU - Kuznetsov, Mikhail A.

AU - Pankova, Alena S.

N1 - Publisher Copyright: © 2022 Elsevier Ltd

PY - 2022/3/30

Y1 - 2022/3/30

N2 - Selectivity of nitrene addition to the C[dbnd]C[sbnd]S[sbnd] fragment depends on the oxidative state of the sulfur atom as has been exemplified on various derivatives of 3,4-dihydro-2H-thiopyran under conditions of oxidative aminoaziridination. A unique structure with 2-thia-7-azabicyclo[4.1.0]heptane-2,2-dioxide core was obtained via addition of nitrene to the C[dbnd]C bond of thiopyran S,S-dioxide. For an unoxidized thiopyran, only en(phthaloyl)hydrazine resulted after cleavage of the initially formed aziridine. S-Oxide trapped the nitrene by the sulfur atom to form the sulfoximine leaving the double bond unaffected.

AB - Selectivity of nitrene addition to the C[dbnd]C[sbnd]S[sbnd] fragment depends on the oxidative state of the sulfur atom as has been exemplified on various derivatives of 3,4-dihydro-2H-thiopyran under conditions of oxidative aminoaziridination. A unique structure with 2-thia-7-azabicyclo[4.1.0]heptane-2,2-dioxide core was obtained via addition of nitrene to the C[dbnd]C bond of thiopyran S,S-dioxide. For an unoxidized thiopyran, only en(phthaloyl)hydrazine resulted after cleavage of the initially formed aziridine. S-Oxide trapped the nitrene by the sulfur atom to form the sulfoximine leaving the double bond unaffected.

KW - Aziridine

KW - N-Aminophthalimide

KW - Nitrene

KW - Sulfone

KW - Sulfoximine

KW - Thiopyran

UR - http://www.scopus.com/inward/record.url?scp=85126350689&partnerID=8YFLogxK

U2 - 10.1016/j.tetlet.2022.153715

DO - 10.1016/j.tetlet.2022.153715

M3 - Article

AN - SCOPUS:85126350689

VL - 94

JO - Tetrahedron Letters

JF - Tetrahedron Letters

SN - 0040-4039

M1 - 153715

ER -

ID: 93941245