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Unusually Reactive Cyclic Anhydride Expands the Scope of the Castagnoli-Cushman Reaction. / Chizhova, Maria; Khoroshilova, Olesya; Dar'In, Dmitry; Krasavin, Mikhail.

в: Journal of Organic Chemistry, Том 83, № 20, 19.10.2018, стр. 12722-12733.

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

Harvard

Chizhova, M, Khoroshilova, O, Dar'In, D & Krasavin, M 2018, 'Unusually Reactive Cyclic Anhydride Expands the Scope of the Castagnoli-Cushman Reaction', Journal of Organic Chemistry, Том. 83, № 20, стр. 12722-12733. https://doi.org/10.1021/acs.joc.8b02164

APA

Chizhova, M., Khoroshilova, O., Dar'In, D., & Krasavin, M. (2018). Unusually Reactive Cyclic Anhydride Expands the Scope of the Castagnoli-Cushman Reaction. Journal of Organic Chemistry, 83(20), 12722-12733. https://doi.org/10.1021/acs.joc.8b02164

Vancouver

Chizhova M, Khoroshilova O, Dar'In D, Krasavin M. Unusually Reactive Cyclic Anhydride Expands the Scope of the Castagnoli-Cushman Reaction. Journal of Organic Chemistry. 2018 Окт. 19;83(20):12722-12733. https://doi.org/10.1021/acs.joc.8b02164

Author

Chizhova, Maria ; Khoroshilova, Olesya ; Dar'In, Dmitry ; Krasavin, Mikhail. / Unusually Reactive Cyclic Anhydride Expands the Scope of the Castagnoli-Cushman Reaction. в: Journal of Organic Chemistry. 2018 ; Том 83, № 20. стр. 12722-12733.

BibTeX

@article{5f8a2b5d598e451e977da1007156be16,
title = "Unusually Reactive Cyclic Anhydride Expands the Scope of the Castagnoli-Cushman Reaction",
abstract = "In the course of synthesizing and testing various {"}azole-including{"} cyclic anhydrides in the Castagnoli-Cushman reaction with imines, a remarkably reactive, pyrrole-based anhydride has been identified. It displayed a remarkably efficient reaction with N-alkyl and N-aryl imines, in particular, with {"}enolizable{"} α-C-H imines which typically fail to react with a majority of known cyclic anhydrides. The reactivity of this anhydride has been justified by an efficient resonance stabilization of its enol form. This finding expands the existing arsenal of highly reactive cyclic anhydrides and further confirms the importance of anhydride enolization for an efficient Castagnoli-Cushman reaction.",
keywords = "HOMOPHTHALIC ANHYDRIDE, DIASTEREOSELECTIVE SYNTHESIS, STEREOSELECTIVE-SYNTHESIS, CYANOSUCCINIC ANHYDRIDES, GAMMA-LACTAMS, ONE-POT, IMINES, ANALOGS, CYCLOADDITION, CONDENSATION",
author = "Maria Chizhova and Olesya Khoroshilova and Dmitry Dar'In and Mikhail Krasavin",
year = "2018",
month = oct,
day = "19",
doi = "10.1021/acs.joc.8b02164",
language = "English",
volume = "83",
pages = "12722--12733",
journal = "Journal of Organic Chemistry",
issn = "0022-3263",
publisher = "American Chemical Society",
number = "20",

}

RIS

TY - JOUR

T1 - Unusually Reactive Cyclic Anhydride Expands the Scope of the Castagnoli-Cushman Reaction

AU - Chizhova, Maria

AU - Khoroshilova, Olesya

AU - Dar'In, Dmitry

AU - Krasavin, Mikhail

PY - 2018/10/19

Y1 - 2018/10/19

N2 - In the course of synthesizing and testing various "azole-including" cyclic anhydrides in the Castagnoli-Cushman reaction with imines, a remarkably reactive, pyrrole-based anhydride has been identified. It displayed a remarkably efficient reaction with N-alkyl and N-aryl imines, in particular, with "enolizable" α-C-H imines which typically fail to react with a majority of known cyclic anhydrides. The reactivity of this anhydride has been justified by an efficient resonance stabilization of its enol form. This finding expands the existing arsenal of highly reactive cyclic anhydrides and further confirms the importance of anhydride enolization for an efficient Castagnoli-Cushman reaction.

AB - In the course of synthesizing and testing various "azole-including" cyclic anhydrides in the Castagnoli-Cushman reaction with imines, a remarkably reactive, pyrrole-based anhydride has been identified. It displayed a remarkably efficient reaction with N-alkyl and N-aryl imines, in particular, with "enolizable" α-C-H imines which typically fail to react with a majority of known cyclic anhydrides. The reactivity of this anhydride has been justified by an efficient resonance stabilization of its enol form. This finding expands the existing arsenal of highly reactive cyclic anhydrides and further confirms the importance of anhydride enolization for an efficient Castagnoli-Cushman reaction.

KW - HOMOPHTHALIC ANHYDRIDE

KW - DIASTEREOSELECTIVE SYNTHESIS

KW - STEREOSELECTIVE-SYNTHESIS

KW - CYANOSUCCINIC ANHYDRIDES

KW - GAMMA-LACTAMS

KW - ONE-POT

KW - IMINES

KW - ANALOGS

KW - CYCLOADDITION

KW - CONDENSATION

UR - http://www.scopus.com/inward/record.url?scp=85054386946&partnerID=8YFLogxK

UR - http://www.mendeley.com/research/unusually-reactive-cyclic-anhydride-expands-scope-castagnolicushman-reaction

U2 - 10.1021/acs.joc.8b02164

DO - 10.1021/acs.joc.8b02164

M3 - Article

AN - SCOPUS:85054386946

VL - 83

SP - 12722

EP - 12733

JO - Journal of Organic Chemistry

JF - Journal of Organic Chemistry

SN - 0022-3263

IS - 20

ER -

ID: 34963981