One-Pot Synthesis of Multifunctionalized 1-Pyrrolines from 2-Alkyl-2 H-azirines and Diazocarbonyl Compounds

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One-Pot Synthesis of Multifunctionalized 1-Pyrrolines from 2-Alkyl-2 H-azirines and Diazocarbonyl Compounds. / Filippov, Ilya P.; Novikov, Mikhail S.; Khlebnikov, Alexander F.; Rostovskii, Nikolai V.

в: Journal of Organic Chemistry, Том 87, № 13, 22.06.2022, стр. 8835-8840.

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

BibTeX

@article{a0c0d77f3d6e40448b802ecfc4867aba,

title = "One-Pot Synthesis of Multifunctionalized 1-Pyrrolines from 2-Alkyl-2 H-azirines and Diazocarbonyl Compounds",

abstract = "A novel strategy for the synthesis of 1-pyrrolines based on formal [4 + 1] annulation of 2-alkyl-2H-azirines with diazocarbonyl compounds has been developed. This one-pot approach includes the Rh(II)-catalyzed formation of 4-alkyl-2-azabuta-1,3-dienes, followed by the DBU-promoted cyclization, and features a good substrate tolerance. The 1-pyrrolines containing an ester group at the C3 were prepared in a three-step one-pot procedure starting from 5-alkoxyisoxazoles. The cyclization of 2-azabutadienes to 1-pyrrolines most likely proceeds via the 6πelectrocyclization of a conjugated NH-azomethine ylide.",

author = "Filippov, {Ilya P.} and Novikov, {Mikhail S.} and Khlebnikov, {Alexander F.} and Rostovskii, {Nikolai V.}",

year = "2022",

month = jun,

day = "22",

doi = "10.1021/acs.joc.2c00977",

language = "English",

volume = "87",

pages = "8835--8840",

journal = "Journal of Organic Chemistry",

issn = "0022-3263",

publisher = "American Chemical Society",

number = "13",

}

RIS

TY - JOUR

T1 - One-Pot Synthesis of Multifunctionalized 1-Pyrrolines from 2-Alkyl-2 H-azirines and Diazocarbonyl Compounds

AU - Filippov, Ilya P.

AU - Novikov, Mikhail S.

AU - Khlebnikov, Alexander F.

AU - Rostovskii, Nikolai V.

PY - 2022/6/22

Y1 - 2022/6/22

N2 - A novel strategy for the synthesis of 1-pyrrolines based on formal [4 + 1] annulation of 2-alkyl-2H-azirines with diazocarbonyl compounds has been developed. This one-pot approach includes the Rh(II)-catalyzed formation of 4-alkyl-2-azabuta-1,3-dienes, followed by the DBU-promoted cyclization, and features a good substrate tolerance. The 1-pyrrolines containing an ester group at the C3 were prepared in a three-step one-pot procedure starting from 5-alkoxyisoxazoles. The cyclization of 2-azabutadienes to 1-pyrrolines most likely proceeds via the 6πelectrocyclization of a conjugated NH-azomethine ylide.

AB - A novel strategy for the synthesis of 1-pyrrolines based on formal [4 + 1] annulation of 2-alkyl-2H-azirines with diazocarbonyl compounds has been developed. This one-pot approach includes the Rh(II)-catalyzed formation of 4-alkyl-2-azabuta-1,3-dienes, followed by the DBU-promoted cyclization, and features a good substrate tolerance. The 1-pyrrolines containing an ester group at the C3 were prepared in a three-step one-pot procedure starting from 5-alkoxyisoxazoles. The cyclization of 2-azabutadienes to 1-pyrrolines most likely proceeds via the 6πelectrocyclization of a conjugated NH-azomethine ylide.

UR - http://www.scopus.com/inward/record.url?scp=85134496754&partnerID=8YFLogxK

UR - https://pubs.acs.org/doi/10.1021/acs.joc.2c00977

UR - https://www.mendeley.com/catalogue/60e7a48c-343a-3fea-8483-483c8b8a58af/

U2 - 10.1021/acs.joc.2c00977

DO - 10.1021/acs.joc.2c00977

M3 - Article

AN - SCOPUS:85134496754

VL - 87

SP - 8835

EP - 8840

JO - Journal of Organic Chemistry

JF - Journal of Organic Chemistry

SN - 0022-3263

IS - 13

ER -

ID: 98575963