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The Castagnoli–Cushman reaction of bicyclic pyrrole dicarboxylic anhydrides bearing electron-withdrawing substituents. / Chizhova, Maria E.; Dar'in, Dmitry V.; Krasavin, Mikhail.

In: Mendeleev Communications , Vol. 30, No. 4, 01.07.2020, p. 496-497.

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

Harvard

Chizhova, ME, Dar'in, DV & Krasavin, M 2020, 'The Castagnoli–Cushman reaction of bicyclic pyrrole dicarboxylic anhydrides bearing electron-withdrawing substituents', Mendeleev Communications , vol. 30, no. 4, pp. 496-497. https://doi.org/10.1016/j.mencom.2020.07.030

APA

Chizhova, M. E., Dar'in, D. V., & Krasavin, M. (2020). The Castagnoli–Cushman reaction of bicyclic pyrrole dicarboxylic anhydrides bearing electron-withdrawing substituents. Mendeleev Communications , 30(4), 496-497. https://doi.org/10.1016/j.mencom.2020.07.030

Vancouver

Chizhova ME, Dar'in DV, Krasavin M. The Castagnoli–Cushman reaction of bicyclic pyrrole dicarboxylic anhydrides bearing electron-withdrawing substituents. Mendeleev Communications . 2020 Jul 1;30(4):496-497. https://doi.org/10.1016/j.mencom.2020.07.030

Author

Chizhova, Maria E. ; Dar'in, Dmitry V. ; Krasavin, Mikhail. / The Castagnoli–Cushman reaction of bicyclic pyrrole dicarboxylic anhydrides bearing electron-withdrawing substituents. In: Mendeleev Communications . 2020 ; Vol. 30, No. 4. pp. 496-497.

BibTeX

@article{e9b9227471ef49dca153cc9bb1fc1f5a,
title = "The Castagnoli–Cushman reaction of bicyclic pyrrole dicarboxylic anhydrides bearing electron-withdrawing substituents",
abstract = "Four anhydrides of 1-(carboxymethyl)pyrrole-2-carboxylic acids bearing electron-withdrawing substituents at positions 6 or 7 of the bicyclic system have been investigated in the Castagnoli–Cushman reaction with imines. 6-Benzoyl- and 7-sulfamoyl-substituted anhydrides demonstrated lower reactivity while 7-benzoyl derivative displayed broader substrate scope. These findings have been rationalized from the mechanistic perspective.",
keywords = "Castagnoli–Cushman reaction, cyclic anhydrides, enolization, imines, resonance stabilization, δ-lactams",
author = "Chizhova, {Maria E.} and Dar'in, {Dmitry V.} and Mikhail Krasavin",
year = "2020",
month = jul,
day = "1",
doi = "10.1016/j.mencom.2020.07.030",
language = "English",
volume = "30",
pages = "496--497",
journal = "Mendeleev Communications",
issn = "0959-9436",
publisher = "Elsevier",
number = "4",

}

RIS

TY - JOUR

T1 - The Castagnoli–Cushman reaction of bicyclic pyrrole dicarboxylic anhydrides bearing electron-withdrawing substituents

AU - Chizhova, Maria E.

AU - Dar'in, Dmitry V.

AU - Krasavin, Mikhail

PY - 2020/7/1

Y1 - 2020/7/1

N2 - Four anhydrides of 1-(carboxymethyl)pyrrole-2-carboxylic acids bearing electron-withdrawing substituents at positions 6 or 7 of the bicyclic system have been investigated in the Castagnoli–Cushman reaction with imines. 6-Benzoyl- and 7-sulfamoyl-substituted anhydrides demonstrated lower reactivity while 7-benzoyl derivative displayed broader substrate scope. These findings have been rationalized from the mechanistic perspective.

AB - Four anhydrides of 1-(carboxymethyl)pyrrole-2-carboxylic acids bearing electron-withdrawing substituents at positions 6 or 7 of the bicyclic system have been investigated in the Castagnoli–Cushman reaction with imines. 6-Benzoyl- and 7-sulfamoyl-substituted anhydrides demonstrated lower reactivity while 7-benzoyl derivative displayed broader substrate scope. These findings have been rationalized from the mechanistic perspective.

KW - Castagnoli–Cushman reaction

KW - cyclic anhydrides

KW - enolization

KW - imines

KW - resonance stabilization

KW - δ-lactams

UR - http://www.scopus.com/inward/record.url?scp=85088948638&partnerID=8YFLogxK

U2 - 10.1016/j.mencom.2020.07.030

DO - 10.1016/j.mencom.2020.07.030

M3 - Article

AN - SCOPUS:85088948638

VL - 30

SP - 496

EP - 497

JO - Mendeleev Communications

JF - Mendeleev Communications

SN - 0959-9436

IS - 4

ER -

ID: 61393843