Reaction of α-Diazopyrroles with Enamines: Synthesis of Pyrrolo[2,1-c][1,2,4]triazines and α-(1,2,5-Triazapenta-1,3-dienyl)pyrroles

Standard

Reaction of α-Diazopyrroles with Enamines: Synthesis of Pyrrolo[2,1-c][1,2,4]triazines and α-(1,2,5-Triazapenta-1,3-dienyl)pyrroles. / Каминский, Никита Андреевич; Галенко, Екатерина Евгениевна ; Новиков, Михаил Сергеевич ; Крюкова, Мария Александровна ; Хлебников, Александр Феодосиевич.

в: Journal of Organic Chemistry, Том 87, № 15, 05.08.2022, стр. 10485-10492.

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

BibTeX

@article{449d1eb468a44569a2f766a1df10008f,

title = "Reaction of α-Diazopyrroles with Enamines: Synthesis of Pyrrolo[2,1-c][1,2,4]triazines and α-(1,2,5-Triazapenta-1,3-dienyl)pyrroles",

abstract = "α-Diazopyrroles selectively react with enamines at room temperature to give either (4+2)-cycloaddition-dehydroamination cascade products, pyrrolo[2,1-c][1,2,4]triazines, or azo coupling products. The reaction was used for the synthesis of functionalized ortho-fused heterocycles with new tetrahydrobenzo[e]pyrrolo[2,1-c][1,2,4]triazine and tetrahydro-6H-cyclohepta[e]pyrrolo[2,1-c][1,2,4]triazine frameworks. Unstable azo compounds, 2-[(2-aminovinyl)diazenyl]pyrroles, were obtained from enamines of tetralone or acyclic ketones. According to the density functional theory calculations, (4+2)-cycloaddition of α-diazopyrroles with enamines proceeds in a nonconcerted manner via the zwitterionic intermediate, which undergoes cyclization to pyrrolotriazine or a competitive 1,5-prototropic shift leading to the formation of azo coupling product.",

author = "Каминский, {Никита Андреевич} and Галенко, {Екатерина Евгениевна} and Новиков, {Михаил Сергеевич} and Крюкова, {Мария Александровна} and Хлебников, {Александр Феодосиевич}",

note = "Publisher Copyright: {\textcopyright} 2022 American Chemical Society.",

year = "2022",

month = aug,

day = "5",

doi = "10.1021/acs.joc.2c01102",

language = "English",

volume = "87",

pages = "10485--10492",

journal = "Journal of Organic Chemistry",

issn = "0022-3263",

publisher = "American Chemical Society",

number = "15",

}

RIS

TY - JOUR

T1 - Reaction of α-Diazopyrroles with Enamines: Synthesis of Pyrrolo[2,1-c][1,2,4]triazines and α-(1,2,5-Triazapenta-1,3-dienyl)pyrroles

AU - Каминский, Никита Андреевич

AU - Галенко, Екатерина Евгениевна

AU - Новиков, Михаил Сергеевич

AU - Крюкова, Мария Александровна

AU - Хлебников, Александр Феодосиевич

PY - 2022/8/5

Y1 - 2022/8/5

N2 - α-Diazopyrroles selectively react with enamines at room temperature to give either (4+2)-cycloaddition-dehydroamination cascade products, pyrrolo[2,1-c][1,2,4]triazines, or azo coupling products. The reaction was used for the synthesis of functionalized ortho-fused heterocycles with new tetrahydrobenzo[e]pyrrolo[2,1-c][1,2,4]triazine and tetrahydro-6H-cyclohepta[e]pyrrolo[2,1-c][1,2,4]triazine frameworks. Unstable azo compounds, 2-[(2-aminovinyl)diazenyl]pyrroles, were obtained from enamines of tetralone or acyclic ketones. According to the density functional theory calculations, (4+2)-cycloaddition of α-diazopyrroles with enamines proceeds in a nonconcerted manner via the zwitterionic intermediate, which undergoes cyclization to pyrrolotriazine or a competitive 1,5-prototropic shift leading to the formation of azo coupling product.

AB - α-Diazopyrroles selectively react with enamines at room temperature to give either (4+2)-cycloaddition-dehydroamination cascade products, pyrrolo[2,1-c][1,2,4]triazines, or azo coupling products. The reaction was used for the synthesis of functionalized ortho-fused heterocycles with new tetrahydrobenzo[e]pyrrolo[2,1-c][1,2,4]triazine and tetrahydro-6H-cyclohepta[e]pyrrolo[2,1-c][1,2,4]triazine frameworks. Unstable azo compounds, 2-[(2-aminovinyl)diazenyl]pyrroles, were obtained from enamines of tetralone or acyclic ketones. According to the density functional theory calculations, (4+2)-cycloaddition of α-diazopyrroles with enamines proceeds in a nonconcerted manner via the zwitterionic intermediate, which undergoes cyclization to pyrrolotriazine or a competitive 1,5-prototropic shift leading to the formation of azo coupling product.

UR - http://www.scopus.com/inward/record.url?scp=85136261331&partnerID=8YFLogxK

UR - https://www.mendeley.com/catalogue/93d07c77-f2c4-34ef-8678-6fb9b410d5d7/

U2 - 10.1021/acs.joc.2c01102

DO - 10.1021/acs.joc.2c01102

M3 - Article

VL - 87

SP - 10485

EP - 10492

JO - Journal of Organic Chemistry

JF - Journal of Organic Chemistry

SN - 0022-3263

IS - 15

ER -

ID: 98529461