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1,3-Dipolar cycloaddition of azomethine ylides derived from imines and difluorocarbene to alkynes : A new active Pb-mediated approach to 2-fluoropyrrole derivatives. / Novikov, Mikhail S.; Khlebnikov, Alexander F.; Sidorina, Elena S.; Kostikov, Rafael R.

в: Journal of the Chemical Society, Perkin Transactions 1, № 2, 2000, стр. 231-237.

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

Harvard

Novikov, MS, Khlebnikov, AF, Sidorina, ES & Kostikov, RR 2000, '1,3-Dipolar cycloaddition of azomethine ylides derived from imines and difluorocarbene to alkynes: A new active Pb-mediated approach to 2-fluoropyrrole derivatives', Journal of the Chemical Society, Perkin Transactions 1, № 2, стр. 231-237. https://doi.org/10.1039/a905518e

APA

Novikov, M. S., Khlebnikov, A. F., Sidorina, E. S., & Kostikov, R. R. (2000). 1,3-Dipolar cycloaddition of azomethine ylides derived from imines and difluorocarbene to alkynes: A new active Pb-mediated approach to 2-fluoropyrrole derivatives. Journal of the Chemical Society, Perkin Transactions 1, (2), 231-237. https://doi.org/10.1039/a905518e

Vancouver

Novikov MS, Khlebnikov AF, Sidorina ES, Kostikov RR. 1,3-Dipolar cycloaddition of azomethine ylides derived from imines and difluorocarbene to alkynes: A new active Pb-mediated approach to 2-fluoropyrrole derivatives. Journal of the Chemical Society, Perkin Transactions 1. 2000;(2):231-237. https://doi.org/10.1039/a905518e

Author

Novikov, Mikhail S. ; Khlebnikov, Alexander F. ; Sidorina, Elena S. ; Kostikov, Rafael R. / 1,3-Dipolar cycloaddition of azomethine ylides derived from imines and difluorocarbene to alkynes : A new active Pb-mediated approach to 2-fluoropyrrole derivatives. в: Journal of the Chemical Society, Perkin Transactions 1. 2000 ; № 2. стр. 231-237.

BibTeX

@article{ab2849b83c0c47858350d2b99377acee,
title = "1,3-Dipolar cycloaddition of azomethine ylides derived from imines and difluorocarbene to alkynes: A new active Pb-mediated approach to 2-fluoropyrrole derivatives",
abstract = "Domino reactions of imines with difluorocarbene in the presence of electron-deficient alkynes lead to 2-fluoropyrrole derivatives. The process involves intermediate azomethine ylide formation, its 1,3-dipolar cycloaddition to alkyne, followed by dehydrofluorination. A modified difluorocarbene generation method using active lead for dibromodifluoromethane reduction is proposed, providing shorter reaction time and improved yields of fluoropyrroles. The reactions with monoactivated acetylenes occur regioselectively. The cycloaddition of ylides to dipolarophiles such as phenylpropynal, whose carbonyl group is more active than the triple bond, gives rise to oxazolidine derivatives, implying a change in the reaction site.",
author = "Novikov, {Mikhail S.} and Khlebnikov, {Alexander F.} and Sidorina, {Elena S.} and Kostikov, {Rafael R.}",
note = "Copyright: Copyright 2018 Elsevier B.V., All rights reserved.",
year = "2000",
doi = "10.1039/a905518e",
language = "English",
pages = "231--237",
journal = "Journal of the Chemical Society, Perkin Transactions 1",
issn = "0300-922X",
publisher = "Chemical Society",
number = "2",

}

RIS

TY - JOUR

T1 - 1,3-Dipolar cycloaddition of azomethine ylides derived from imines and difluorocarbene to alkynes

T2 - A new active Pb-mediated approach to 2-fluoropyrrole derivatives

AU - Novikov, Mikhail S.

AU - Khlebnikov, Alexander F.

AU - Sidorina, Elena S.

AU - Kostikov, Rafael R.

N1 - Copyright: Copyright 2018 Elsevier B.V., All rights reserved.

PY - 2000

Y1 - 2000

N2 - Domino reactions of imines with difluorocarbene in the presence of electron-deficient alkynes lead to 2-fluoropyrrole derivatives. The process involves intermediate azomethine ylide formation, its 1,3-dipolar cycloaddition to alkyne, followed by dehydrofluorination. A modified difluorocarbene generation method using active lead for dibromodifluoromethane reduction is proposed, providing shorter reaction time and improved yields of fluoropyrroles. The reactions with monoactivated acetylenes occur regioselectively. The cycloaddition of ylides to dipolarophiles such as phenylpropynal, whose carbonyl group is more active than the triple bond, gives rise to oxazolidine derivatives, implying a change in the reaction site.

AB - Domino reactions of imines with difluorocarbene in the presence of electron-deficient alkynes lead to 2-fluoropyrrole derivatives. The process involves intermediate azomethine ylide formation, its 1,3-dipolar cycloaddition to alkyne, followed by dehydrofluorination. A modified difluorocarbene generation method using active lead for dibromodifluoromethane reduction is proposed, providing shorter reaction time and improved yields of fluoropyrroles. The reactions with monoactivated acetylenes occur regioselectively. The cycloaddition of ylides to dipolarophiles such as phenylpropynal, whose carbonyl group is more active than the triple bond, gives rise to oxazolidine derivatives, implying a change in the reaction site.

UR - http://www.scopus.com/inward/record.url?scp=0034695708&partnerID=8YFLogxK

U2 - 10.1039/a905518e

DO - 10.1039/a905518e

M3 - Article

SP - 231

EP - 237

JO - Journal of the Chemical Society, Perkin Transactions 1

JF - Journal of the Chemical Society, Perkin Transactions 1

SN - 0300-922X

IS - 2

ER -

ID: 5057044