Standard

Synthesis of 3,4-Bis(hydroxymethyl)-2,2,5,5-tetraethylpyrrolidin-1-oxyl via 1,3-Dipolar Cycloaddition of Azomethine Ylide to Activated Alkene. / Dobrynin, Sergey A.; Glazachev, Yuri I.; Gatilov, Yuri V. et al.

In: Journal of Organic Chemistry, Vol. 83, No. 10, 18.05.2018, p. 5392-5397.

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

Harvard

Dobrynin, SA, Glazachev, YI, Gatilov, YV, Chernyak, EI, Salnikov, GE & Kirilyuk, IA 2018, 'Synthesis of 3,4-Bis(hydroxymethyl)-2,2,5,5-tetraethylpyrrolidin-1-oxyl via 1,3-Dipolar Cycloaddition of Azomethine Ylide to Activated Alkene', Journal of Organic Chemistry, vol. 83, no. 10, pp. 5392-5397. https://doi.org/10.1021/acs.joc.8b00085

APA

Dobrynin, S. A., Glazachev, Y. I., Gatilov, Y. V., Chernyak, E. I., Salnikov, G. E., & Kirilyuk, I. A. (2018). Synthesis of 3,4-Bis(hydroxymethyl)-2,2,5,5-tetraethylpyrrolidin-1-oxyl via 1,3-Dipolar Cycloaddition of Azomethine Ylide to Activated Alkene. Journal of Organic Chemistry, 83(10), 5392-5397. https://doi.org/10.1021/acs.joc.8b00085

Vancouver

Dobrynin SA, Glazachev YI, Gatilov YV, Chernyak EI, Salnikov GE, Kirilyuk IA. Synthesis of 3,4-Bis(hydroxymethyl)-2,2,5,5-tetraethylpyrrolidin-1-oxyl via 1,3-Dipolar Cycloaddition of Azomethine Ylide to Activated Alkene. Journal of Organic Chemistry. 2018 May 18;83(10):5392-5397. doi: 10.1021/acs.joc.8b00085

Author

Dobrynin, Sergey A. ; Glazachev, Yuri I. ; Gatilov, Yuri V. et al. / Synthesis of 3,4-Bis(hydroxymethyl)-2,2,5,5-tetraethylpyrrolidin-1-oxyl via 1,3-Dipolar Cycloaddition of Azomethine Ylide to Activated Alkene. In: Journal of Organic Chemistry. 2018 ; Vol. 83, No. 10. pp. 5392-5397.

BibTeX

@article{53e4cb30576a42648779d4c90a51a1fa,
title = "Synthesis of 3,4-Bis(hydroxymethyl)-2,2,5,5-tetraethylpyrrolidin-1-oxyl via 1,3-Dipolar Cycloaddition of Azomethine Ylide to Activated Alkene",
abstract = "A simple method for the synthesis of sterically shielded pyrrolidine nitroxides, including the title compound, has been suggested. The key procedure implies assembling the pyrrolidine ring from α-amino acid, ketone, and activated alkene in a three-component domino process, followed by oxidation to nitrone and Grignard reagent addition. The new nitroxides demonstrate very high stability against reduction with ascorbate.",
keywords = "IN-VIVO EVALUATION, REDUCTION KINETICS, SPIN LABELS, CELL EPR, NITROXIDES, STABILITY, GLUTATHIONE, PYRROLINE, RADICALS, SERIES",
author = "Dobrynin, {Sergey A.} and Glazachev, {Yuri I.} and Gatilov, {Yuri V.} and Chernyak, {Elena I.} and Salnikov, {George E.} and Kirilyuk, {Igor A.}",
note = "Publisher Copyright: {\textcopyright} 2018 American Chemical Society.",
year = "2018",
month = may,
day = "18",
doi = "10.1021/acs.joc.8b00085",
language = "English",
volume = "83",
pages = "5392--5397",
journal = "Journal of Organic Chemistry",
issn = "0022-3263",
publisher = "American Chemical Society",
number = "10",

}

RIS

TY - JOUR

T1 - Synthesis of 3,4-Bis(hydroxymethyl)-2,2,5,5-tetraethylpyrrolidin-1-oxyl via 1,3-Dipolar Cycloaddition of Azomethine Ylide to Activated Alkene

AU - Dobrynin, Sergey A.

AU - Glazachev, Yuri I.

AU - Gatilov, Yuri V.

AU - Chernyak, Elena I.

AU - Salnikov, George E.

AU - Kirilyuk, Igor A.

N1 - Publisher Copyright: © 2018 American Chemical Society.

PY - 2018/5/18

Y1 - 2018/5/18

N2 - A simple method for the synthesis of sterically shielded pyrrolidine nitroxides, including the title compound, has been suggested. The key procedure implies assembling the pyrrolidine ring from α-amino acid, ketone, and activated alkene in a three-component domino process, followed by oxidation to nitrone and Grignard reagent addition. The new nitroxides demonstrate very high stability against reduction with ascorbate.

AB - A simple method for the synthesis of sterically shielded pyrrolidine nitroxides, including the title compound, has been suggested. The key procedure implies assembling the pyrrolidine ring from α-amino acid, ketone, and activated alkene in a three-component domino process, followed by oxidation to nitrone and Grignard reagent addition. The new nitroxides demonstrate very high stability against reduction with ascorbate.

KW - IN-VIVO EVALUATION

KW - REDUCTION KINETICS

KW - SPIN LABELS

KW - CELL EPR

KW - NITROXIDES

KW - STABILITY

KW - GLUTATHIONE

KW - PYRROLINE

KW - RADICALS

KW - SERIES

UR - http://www.scopus.com/inward/record.url?scp=85046405890&partnerID=8YFLogxK

U2 - 10.1021/acs.joc.8b00085

DO - 10.1021/acs.joc.8b00085

M3 - Article

C2 - 29668276

AN - SCOPUS:85046405890

VL - 83

SP - 5392

EP - 5397

JO - Journal of Organic Chemistry

JF - Journal of Organic Chemistry

SN - 0022-3263

IS - 10

ER -

ID: 13541609