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Oxidative [3+2]Cycloaddition of Alkynylphosphonates with Heterocyclic N-Imines: Synthesis of Pyrazolo[1,5-a]Pyridine-3-phosphonates. / Philippov, Igor; Gatilov, Yuriy; Sonina, Alina et al.

In: Molecules, Vol. 27, No. 22, 7913, 11.2022.

Research output: Contribution to journal › Article › peer-review

Harvard

Philippov, I, Gatilov, Y, Sonina, A & Vorob’ev, A 2022, 'Oxidative [3+2]Cycloaddition of Alkynylphosphonates with Heterocyclic N-Imines: Synthesis of Pyrazolo[1,5-a]Pyridine-3-phosphonates', Molecules, vol. 27, no. 22, 7913. https://doi.org/10.3390/molecules27227913

APA

Philippov, I., Gatilov, Y., Sonina, A., & Vorob’ev, A. (2022). Oxidative [3+2]Cycloaddition of Alkynylphosphonates with Heterocyclic N-Imines: Synthesis of Pyrazolo[1,5-a]Pyridine-3-phosphonates. Molecules, 27(22), [7913]. https://doi.org/10.3390/molecules27227913

Vancouver

Philippov I, Gatilov Y, Sonina A, Vorob’ev A. Oxidative [3+2]Cycloaddition of Alkynylphosphonates with Heterocyclic N-Imines: Synthesis of Pyrazolo[1,5-a]Pyridine-3-phosphonates. Molecules. 2022 Nov;27(22):7913. doi: 10.3390/molecules27227913

Author

Philippov, Igor ; Gatilov, Yuriy ; Sonina, Alina et al. / Oxidative [3+2]Cycloaddition of Alkynylphosphonates with Heterocyclic N-Imines: Synthesis of Pyrazolo[1,5-a]Pyridine-3-phosphonates. In: Molecules. 2022 ; Vol. 27, No. 22.

BibTeX

@article{913e1847c1df4ad2af70c63465541b5f,
title = "Oxidative [3+2]Cycloaddition of Alkynylphosphonates with Heterocyclic N-Imines: Synthesis of Pyrazolo[1,5-a]Pyridine-3-phosphonates",
abstract = "A series of pyrazolo[1,5-a]pyridine-3-ylphosphonates were prepared with moderate to good yields by the oxidative [3+2]cycloaddition of 2-subtituted ethynylphosphonates with in situ generated pyridinium-N-imines and their annulated analogs. 2-Aliphatic and 2-Ph acetylenes demonstrate low activity, and the corresponding pyrazolopyridines were achieved with a moderate yield in the presence of 10 mol% Fe(NO3)3·9H2O. At the same time, tetraethyl ethynylbisphosphonate, diethyl 2-TMS- and 2-OPh-ethynylphosphonates possess much greater reactivity and the corresponding pyrazolo[1,5-a]pyridines, and their annulated derivatives were obtained with good to excellent yields without any catalyst. 2-Halogenated ethynylphosphonates also readily reacted with pyridinium-N-imines, forming complex mixtures containing poor amounts of 2-halogenated pyrazolopyridines.",
keywords = "alkynes, cycloaddition, heterocycles, iron, oxidation, Organophosphonates, Pyridines, Imines, Oxidative Stress, Molecular Structure, Cycloaddition Reaction",
author = "Igor Philippov and Yuriy Gatilov and Alina Sonina and Aleksey Vorob{\textquoteright}ev",
note = "Funding Information: This research was funded by the Ministry of Science and Education of Russian Federation, grant number 122040800262-9. Publisher Copyright: {\textcopyright} 2022 by the authors.",
year = "2022",
month = nov,
doi = "10.3390/molecules27227913",
language = "English",
volume = "27",
journal = "Molecules",
issn = "1420-3049",
publisher = "Multidisciplinary Digital Publishing Institute (MDPI)",
number = "22",

}

RIS

TY - JOUR

T1 - Oxidative [3+2]Cycloaddition of Alkynylphosphonates with Heterocyclic N-Imines: Synthesis of Pyrazolo[1,5-a]Pyridine-3-phosphonates

AU - Philippov, Igor

AU - Gatilov, Yuriy

AU - Sonina, Alina

AU - Vorob’ev, Aleksey

N1 - Funding Information: This research was funded by the Ministry of Science and Education of Russian Federation, grant number 122040800262-9. Publisher Copyright: © 2022 by the authors.

PY - 2022/11

Y1 - 2022/11

N2 - A series of pyrazolo[1,5-a]pyridine-3-ylphosphonates were prepared with moderate to good yields by the oxidative [3+2]cycloaddition of 2-subtituted ethynylphosphonates with in situ generated pyridinium-N-imines and their annulated analogs. 2-Aliphatic and 2-Ph acetylenes demonstrate low activity, and the corresponding pyrazolopyridines were achieved with a moderate yield in the presence of 10 mol% Fe(NO3)3·9H2O. At the same time, tetraethyl ethynylbisphosphonate, diethyl 2-TMS- and 2-OPh-ethynylphosphonates possess much greater reactivity and the corresponding pyrazolo[1,5-a]pyridines, and their annulated derivatives were obtained with good to excellent yields without any catalyst. 2-Halogenated ethynylphosphonates also readily reacted with pyridinium-N-imines, forming complex mixtures containing poor amounts of 2-halogenated pyrazolopyridines.

AB - A series of pyrazolo[1,5-a]pyridine-3-ylphosphonates were prepared with moderate to good yields by the oxidative [3+2]cycloaddition of 2-subtituted ethynylphosphonates with in situ generated pyridinium-N-imines and their annulated analogs. 2-Aliphatic and 2-Ph acetylenes demonstrate low activity, and the corresponding pyrazolopyridines were achieved with a moderate yield in the presence of 10 mol% Fe(NO3)3·9H2O. At the same time, tetraethyl ethynylbisphosphonate, diethyl 2-TMS- and 2-OPh-ethynylphosphonates possess much greater reactivity and the corresponding pyrazolo[1,5-a]pyridines, and their annulated derivatives were obtained with good to excellent yields without any catalyst. 2-Halogenated ethynylphosphonates also readily reacted with pyridinium-N-imines, forming complex mixtures containing poor amounts of 2-halogenated pyrazolopyridines.

KW - alkynes

KW - cycloaddition

KW - heterocycles

KW - iron

KW - oxidation

KW - Organophosphonates

KW - Pyridines

KW - Imines

KW - Oxidative Stress

KW - Molecular Structure

KW - Cycloaddition Reaction

UR - http://www.scopus.com/inward/record.url?scp=85142616905&partnerID=8YFLogxK

UR - https://www.mendeley.com/catalogue/3b14fa31-91ec-3d06-9b15-0d0d62d91fc7/

U2 - 10.3390/molecules27227913

DO - 10.3390/molecules27227913

M3 - Article

C2 - 36432015

AN - SCOPUS:85142616905

VL - 27

JO - Molecules

JF - Molecules

SN - 1420-3049

IS - 22

M1 - 7913

ER -

ID: 40001348