Thermal Ring Expansion of 2-Sulfonylimidoyl-1-phthalimidoaziridines into N-Sulfonylimidazoles

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Thermal Ring Expansion of 2-Sulfonylimidoyl-1-phthalimidoaziridines into N-Sulfonylimidazoles. / Стукалов, Александр Юрьевич; Суслонов, Виталий Валерьевич; Кузнецов, Михаил Анатольевич.

In: European Journal of Organic Chemistry, Vol. 2018, No. 14, 17.04.2018, p. 1634-1645.

Research output: Contribution to journal › Article › peer-review

BibTeX

@article{9537d73297b64769a52f571a6e092489,

title = "Thermal Ring Expansion of 2-Sulfonylimidoyl-1-phthalimidoaziridines into N-Sulfonylimidazoles",

abstract = "The oxidative phthalimidoaziridination of conjugated unsaturated N-sulfonylimines leads, in most cases, to di-substituted, tri-substituted and spiro-fused imidoylaziridines in synthetically useful yields typically above 70 %. The latter are thermally transformed into di-substituted, tri-substituted, and condensed N-sulfonylimidazoles. Interestingly, this ring expansion is accompanied by an intramolecular 1,3-sulfonyl shift from one nitrogen atom to another.",

keywords = "окислительное аминоазиридинирование, Aziridines, Imidazoles, Nitrogen heterocycles, Ring expansion, Sulfonyl migration, Synthetic methods, VINYL AZIRIDINES, ISOMERIZATION, EFFICIENT SYNTHESIS, IMIDAZOLES, ANTITUMOR-ACTIVITY, REARRANGEMENT, HEINE REACTION, LEWIS-ACIDS, IONIC LIQUIDS, DERIVATIVES",

author = "Стукалов, {Александр Юрьевич} and Суслонов, {Виталий Валерьевич} and Кузнецов, {Михаил Анатольевич}",

note = "окислительное фталимидоазиридинированиесопряженных N-сульфонилазиридинов, как правило, приводит к имидоилазиридинам с выходами более 70%",

year = "2018",

month = apr,

day = "17",

doi = "10.1002/ejoc.201701806",

language = "English",

volume = "2018",

pages = "1634--1645",

journal = "European Journal of Organic Chemistry",

issn = "1434-193X",

publisher = "Wiley-Blackwell",

number = "14",

}

RIS

TY - JOUR

T1 - Thermal Ring Expansion of 2-Sulfonylimidoyl-1-phthalimidoaziridines into N-Sulfonylimidazoles

AU - Стукалов, Александр Юрьевич

AU - Суслонов, Виталий Валерьевич

AU - Кузнецов, Михаил Анатольевич

N1 - окислительное фталимидоазиридинированиесопряженных N-сульфонилазиридинов, как правило, приводит к имидоилазиридинам с выходами более 70%

PY - 2018/4/17

Y1 - 2018/4/17

N2 - The oxidative phthalimidoaziridination of conjugated unsaturated N-sulfonylimines leads, in most cases, to di-substituted, tri-substituted and spiro-fused imidoylaziridines in synthetically useful yields typically above 70 %. The latter are thermally transformed into di-substituted, tri-substituted, and condensed N-sulfonylimidazoles. Interestingly, this ring expansion is accompanied by an intramolecular 1,3-sulfonyl shift from one nitrogen atom to another.

AB - The oxidative phthalimidoaziridination of conjugated unsaturated N-sulfonylimines leads, in most cases, to di-substituted, tri-substituted and spiro-fused imidoylaziridines in synthetically useful yields typically above 70 %. The latter are thermally transformed into di-substituted, tri-substituted, and condensed N-sulfonylimidazoles. Interestingly, this ring expansion is accompanied by an intramolecular 1,3-sulfonyl shift from one nitrogen atom to another.

KW - окислительное аминоазиридинирование

KW - Aziridines

KW - Imidazoles

KW - Nitrogen heterocycles

KW - Ring expansion

KW - Sulfonyl migration

KW - Synthetic methods

KW - VINYL AZIRIDINES

KW - ISOMERIZATION

KW - EFFICIENT SYNTHESIS

KW - IMIDAZOLES

KW - ANTITUMOR-ACTIVITY

KW - REARRANGEMENT

KW - HEINE REACTION

KW - LEWIS-ACIDS

KW - IONIC LIQUIDS

KW - DERIVATIVES

UR - http://www.scopus.com/inward/record.url?scp=85045662628&partnerID=8YFLogxK

UR - http://www.mendeley.com/research/thermal-ring-expansion-2sulfonylimidoyl1phthalimidoaziridines-nsulfonylimidazoles

U2 - 10.1002/ejoc.201701806

DO - 10.1002/ejoc.201701806

M3 - Article

VL - 2018

SP - 1634

EP - 1645

JO - European Journal of Organic Chemistry

JF - European Journal of Organic Chemistry

SN - 1434-193X

IS - 14

ER -

ID: 35787330