Synthesis of 3‐Alkoxy-4-Pyrrolin-2-ones via Rhodium(II)-Catalyzed Denitrogenative Transannulation of 1H‐1,2,3-Triazoles with Diazo Esters

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Synthesis of 3‐Alkoxy-4-Pyrrolin-2-ones via Rhodium(II)-Catalyzed Denitrogenative Transannulation of 1H‐1,2,3-Triazoles with Diazo Esters. / Коронатов, Александр Николаевич ; Ростовский, Николай Витальевич ; Хлебников, Александр Феодосиевич ; Новиков, Михаил Сергеевич.

в: Organic Letters, Том 22, № 20, 16.10.2020, стр. 7958–7963.

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

BibTeX

@article{8ff5193232844d03bf89f45120f90ef9,

title = "Synthesis of 3‐Alkoxy-4-Pyrrolin-2-ones via Rhodium(II)-Catalyzed Denitrogenative Transannulation of 1H‐1,2,3-Triazoles with Diazo Esters",

abstract = "A method for the synthesis of densely substituted 4-pyrrolin-2-ones by Rh(II)-catalyzed denitrogenative transannulation of 1-alkyl-4-aryl-1H-1,2,3-triazoles with diazo esters has been developed. The reaction proceeds via an attack of the rhodium-bound carbene at the N2 atom of the triazole and the formation of unstable 3,4-dihydro-1,2,4-triazine, which further undergoes ring contraction to a 4-pyrrolin-2-one under rhodium catalysis. The method is inapplicable to 1,2,3-triazoles with primary alkyl substituent at C4, which afford stable 1,2,3-triazol-3-ium ylides as the main products.",

author = "Коронатов, {Александр Николаевич} and Ростовский, {Николай Витальевич} and Хлебников, {Александр Феодосиевич} and Новиков, {Михаил Сергеевич}",

note = "Publisher Copyright: {\textcopyright} 2020 American Chemical Society.",

year = "2020",

month = oct,

day = "16",

doi = "10.1021/acs.orglett.0c02893",

language = "English",

volume = "22",

pages = "7958–7963",

journal = "Organic Letters",

issn = "1523-7060",

publisher = "American Chemical Society",

number = "20",

}

RIS

TY - JOUR

T1 - Synthesis of 3‐Alkoxy-4-Pyrrolin-2-ones via Rhodium(II)-Catalyzed Denitrogenative Transannulation of 1H‐1,2,3-Triazoles with Diazo Esters

AU - Коронатов, Александр Николаевич

AU - Ростовский, Николай Витальевич

AU - Хлебников, Александр Феодосиевич

AU - Новиков, Михаил Сергеевич

PY - 2020/10/16

Y1 - 2020/10/16

N2 - A method for the synthesis of densely substituted 4-pyrrolin-2-ones by Rh(II)-catalyzed denitrogenative transannulation of 1-alkyl-4-aryl-1H-1,2,3-triazoles with diazo esters has been developed. The reaction proceeds via an attack of the rhodium-bound carbene at the N2 atom of the triazole and the formation of unstable 3,4-dihydro-1,2,4-triazine, which further undergoes ring contraction to a 4-pyrrolin-2-one under rhodium catalysis. The method is inapplicable to 1,2,3-triazoles with primary alkyl substituent at C4, which afford stable 1,2,3-triazol-3-ium ylides as the main products.

AB - A method for the synthesis of densely substituted 4-pyrrolin-2-ones by Rh(II)-catalyzed denitrogenative transannulation of 1-alkyl-4-aryl-1H-1,2,3-triazoles with diazo esters has been developed. The reaction proceeds via an attack of the rhodium-bound carbene at the N2 atom of the triazole and the formation of unstable 3,4-dihydro-1,2,4-triazine, which further undergoes ring contraction to a 4-pyrrolin-2-one under rhodium catalysis. The method is inapplicable to 1,2,3-triazoles with primary alkyl substituent at C4, which afford stable 1,2,3-triazol-3-ium ylides as the main products.

UR - http://www.scopus.com/inward/record.url?scp=85093538509&partnerID=8YFLogxK

UR - https://www.mendeley.com/catalogue/80ce0066-fadb-3338-a682-9b1db1b665e2/

U2 - 10.1021/acs.orglett.0c02893

DO - 10.1021/acs.orglett.0c02893

M3 - Article

VL - 22

SP - 7958

EP - 7963

JO - Organic Letters

JF - Organic Letters

SN - 1523-7060

IS - 20

ER -

ID: 70360850