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Isoxazole strategy for the synthesis of α-aminopyrrole derivatives. / Galenko, Ekaterina E.; Linnik, Stanislav A.; Khoroshilova, Olesya V.; Novikov, Mikhail Sergeevich; Khlebnikov, Alexander F.

в: The Journal of organic chemistry, Том 84, № 17, 06.09.2019, стр. 11275-11285.

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

Harvard

Galenko, EE, Linnik, SA, Khoroshilova, OV, Novikov, MS & Khlebnikov, AF 2019, 'Isoxazole strategy for the synthesis of α-aminopyrrole derivatives', The Journal of organic chemistry, Том. 84, № 17, стр. 11275-11285. https://doi.org/10.1021/acs.joc.9b01634

APA

Galenko, E. E., Linnik, S. A., Khoroshilova, O. V., Novikov, M. S., & Khlebnikov, A. F. (2019). Isoxazole strategy for the synthesis of α-aminopyrrole derivatives. The Journal of organic chemistry, 84(17), 11275-11285. https://doi.org/10.1021/acs.joc.9b01634

Vancouver

Galenko EE, Linnik SA, Khoroshilova OV, Novikov MS, Khlebnikov AF. Isoxazole strategy for the synthesis of α-aminopyrrole derivatives. The Journal of organic chemistry. 2019 Сент. 6;84(17):11275-11285. https://doi.org/10.1021/acs.joc.9b01634

Author

Galenko, Ekaterina E. ; Linnik, Stanislav A. ; Khoroshilova, Olesya V. ; Novikov, Mikhail Sergeevich ; Khlebnikov, Alexander F. / Isoxazole strategy for the synthesis of α-aminopyrrole derivatives. в: The Journal of organic chemistry. 2019 ; Том 84, № 17. стр. 11275-11285.

BibTeX

@article{6999b1ec14b3428aabf2f6120c7a1dcb,
title = "Isoxazole strategy for the synthesis of α-aminopyrrole derivatives",
abstract = "A synthesis of methyl 5-aminopyrrole-3-carboxylates from 4-methyleneisoxazol-3-ones via “cyanide Michael addition/methylation/reductive isoxazole-pyrrole transformation” is developed. The last step occurs in a domino mode involving Mo(CO)6-mediated reductive isoxazole ring-opening, Mo(CO)6-catalyzed cis-trans-isomerization of the enamine intermediate followed by 1,5-exo-dig cyclization. 5-Amino-1H-pyrrolo-3-carboxylates react with 1,3-diketones, affording pyrrolo[1,2-a]pyrimidine-7-carboxylates, and are easily converted into 2-diazo-2H-pyrrole-4-carboxylates. These compounds demonstrate the reactivity of both diazo compounds, giving pyrrole-containing products of intra/intermolecular azo coupling, and carbenes to give pyrrole-containing insertion products into CH and OH bonds under photolysis.",
keywords = "ONE-STEP SYNTHESIS, PYRROLE DERIVATIVES, AMINES, RING, CYCLIZATION, NITRILES, CONDENSATION, HETEROCYCLES, AGENTS",
author = "Galenko, {Ekaterina E.} and Linnik, {Stanislav A.} and Khoroshilova, {Olesya V.} and Novikov, {Mikhail Sergeevich} and Khlebnikov, {Alexander F.}",
note = "Publisher Copyright: {\textcopyright} 2019 American Chemical Society.",
year = "2019",
month = sep,
day = "6",
doi = "10.1021/acs.joc.9b01634",
language = "English",
volume = "84",
pages = "11275--11285",
journal = "Journal of Organic Chemistry",
issn = "0022-3263",
publisher = "American Chemical Society",
number = "17",

}

RIS

TY - JOUR

T1 - Isoxazole strategy for the synthesis of α-aminopyrrole derivatives

AU - Galenko, Ekaterina E.

AU - Linnik, Stanislav A.

AU - Khoroshilova, Olesya V.

AU - Novikov, Mikhail Sergeevich

AU - Khlebnikov, Alexander F.

N1 - Publisher Copyright: © 2019 American Chemical Society.

PY - 2019/9/6

Y1 - 2019/9/6

N2 - A synthesis of methyl 5-aminopyrrole-3-carboxylates from 4-methyleneisoxazol-3-ones via “cyanide Michael addition/methylation/reductive isoxazole-pyrrole transformation” is developed. The last step occurs in a domino mode involving Mo(CO)6-mediated reductive isoxazole ring-opening, Mo(CO)6-catalyzed cis-trans-isomerization of the enamine intermediate followed by 1,5-exo-dig cyclization. 5-Amino-1H-pyrrolo-3-carboxylates react with 1,3-diketones, affording pyrrolo[1,2-a]pyrimidine-7-carboxylates, and are easily converted into 2-diazo-2H-pyrrole-4-carboxylates. These compounds demonstrate the reactivity of both diazo compounds, giving pyrrole-containing products of intra/intermolecular azo coupling, and carbenes to give pyrrole-containing insertion products into CH and OH bonds under photolysis.

AB - A synthesis of methyl 5-aminopyrrole-3-carboxylates from 4-methyleneisoxazol-3-ones via “cyanide Michael addition/methylation/reductive isoxazole-pyrrole transformation” is developed. The last step occurs in a domino mode involving Mo(CO)6-mediated reductive isoxazole ring-opening, Mo(CO)6-catalyzed cis-trans-isomerization of the enamine intermediate followed by 1,5-exo-dig cyclization. 5-Amino-1H-pyrrolo-3-carboxylates react with 1,3-diketones, affording pyrrolo[1,2-a]pyrimidine-7-carboxylates, and are easily converted into 2-diazo-2H-pyrrole-4-carboxylates. These compounds demonstrate the reactivity of both diazo compounds, giving pyrrole-containing products of intra/intermolecular azo coupling, and carbenes to give pyrrole-containing insertion products into CH and OH bonds under photolysis.

KW - ONE-STEP SYNTHESIS

KW - PYRROLE DERIVATIVES

KW - AMINES

KW - RING

KW - CYCLIZATION

KW - NITRILES

KW - CONDENSATION

KW - HETEROCYCLES

KW - AGENTS

UR - http://www.mendeley.com/research/isoxazole-strategy-synthesis-%CE%B1aminopyrrole-derivatives

UR - https://pubs.acs.org/doi/10.1021/acs.joc.9b01634

UR - http://www.scopus.com/inward/record.url?scp=85071953601&partnerID=8YFLogxK

U2 - 10.1021/acs.joc.9b01634

DO - 10.1021/acs.joc.9b01634

M3 - Article

VL - 84

SP - 11275

EP - 11285

JO - Journal of Organic Chemistry

JF - Journal of Organic Chemistry

SN - 0022-3263

IS - 17

ER -

ID: 45063828