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 › рецензирование

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

Другие файлы и ссылки

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

@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 › рецензирование

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 -