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

Sergey A. Dobrynin; Yuri I. Glazachev; Yuri V. Gatilov; Elena I. Chernyak; George E. Salnikov; Igor A. Kirilyuk

doi:10.1021/acs.joc.8b00085

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

Sergey A. Dobrynin, Yuri I. Glazachev, Yuri V. Gatilov, Elena I. Chernyak, George E. Salnikov, Igor A. Kirilyuk

Результат исследования: Научные публикации в периодических изданиях › статья

8 Цитирования (Scopus)

Аннотация

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.

Язык оригинала	английский
Страницы (с-по)	5392-5397
Число страниц	6
Журнал	Journal of Organic Chemistry
Том	83
Номер выпуска	10
DOI	https://doi.org/10.1021/acs.joc.8b00085
Состояние	Опубликовано - 18 мая 2018

Доступ к документу

10.1021/acs.joc.8b00085

Link to publication in Scopus

Fingerprint Подробные сведения о темах исследования «Synthesis of 3,4-Bis(hydroxymethyl)-2,2,5,5-tetraethylpyrrolidin-1-oxyl via 1,3-Dipolar Cycloaddition of Azomethine Ylide to Activated Alkene». Вместе они формируют уникальный семантический отпечаток (fingerprint).

Цитировать

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

@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.}",

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",

}

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.; Chernyak, Elena I.; Salnikov, George E.; Kirilyuk, Igor A.

В: Journal of Organic Chemistry, Том 83, № 10, 18.05.2018, стр. 5392-5397.

Результат исследования: Научные публикации в периодических изданиях › статья

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.

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 -