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Steric hindrances to the cycloaddition of (Z)-1-arylmethylidene-5,5-dimethyl-3-oxopyrazolidin-1-ium-2-ides to N-arylmaleimides. / Koptelov, Y.B.; Antuganov, D.O.; Molchanov, A.P.; Kostikov, R.R.

In: Russian Journal of Organic Chemistry, No. 7, 2015, p. 972-981.

Research output: Contribution to journal › Article

Harvard

Koptelov, YB, Antuganov, DO, Molchanov, AP & Kostikov, RR 2015, 'Steric hindrances to the cycloaddition of (Z)-1-arylmethylidene-5,5-dimethyl-3-oxopyrazolidin-1-ium-2-ides to N-arylmaleimides', Russian Journal of Organic Chemistry, no. 7, pp. 972-981. https://doi.org/10.1134/S1070428015070143

APA

Koptelov, Y. B., Antuganov, D. O., Molchanov, A. P., & Kostikov, R. R. (2015). Steric hindrances to the cycloaddition of (Z)-1-arylmethylidene-5,5-dimethyl-3-oxopyrazolidin-1-ium-2-ides to N-arylmaleimides. Russian Journal of Organic Chemistry, (7), 972-981. https://doi.org/10.1134/S1070428015070143

Vancouver

Koptelov YB, Antuganov DO, Molchanov AP, Kostikov RR. Steric hindrances to the cycloaddition of (Z)-1-arylmethylidene-5,5-dimethyl-3-oxopyrazolidin-1-ium-2-ides to N-arylmaleimides. Russian Journal of Organic Chemistry. 2015;(7):972-981. https://doi.org/10.1134/S1070428015070143

Author

Koptelov, Y.B. ; Antuganov, D.O. ; Molchanov, A.P. ; Kostikov, R.R. / Steric hindrances to the cycloaddition of (Z)-1-arylmethylidene-5,5-dimethyl-3-oxopyrazolidin-1-ium-2-ides to N-arylmaleimides. In: Russian Journal of Organic Chemistry. 2015 ; No. 7. pp. 972-981.

BibTeX

@article{057899daa4c3402eb7fd6ff120969001,
title = "Steric hindrances to the cycloaddition of (Z)-1-arylmethylidene-5,5-dimethyl-3-oxopyrazolidin-1-ium-2-ides to N-arylmaleimides",
abstract = "{\textcopyright} 2015 Pleiades Publishing, Ltd.Sterically hindered cycloaddition of (Z)-1-arylmethylidene-5,5-dimethyl-3-oxopyrazolidin-1-ium-2-ides to 4-mono- and 2,6-disubstituted N-arylmaleimides requires prolonged heating (40-60 h) at ~150-155°C and yields mixtures of diastereoisomeric cycloadducts. The observed diastereoselectivity is determined by both electronic and steric interactions, depending on the nature and position of substituents in the azomethine imine and maleimide. The reactions of (Z)-1-(2,6-dichlorobenzylidene)-5,5-dimethyl-3-oxopyrazolidin-1-ium-2-ide with 4-substituted N-arylmaleimides give mainly the corresponding cis adducts as a result of preferential exo attack by the dipolarophile, whereas trans adducts predominate in the cycloaddition of (Z)-1-(4-X-benzylidene)-5,5-dimethyl-3-oxopyrazolidin-1-ium-2-ide and (Z)-1-(2,6-dichlorobenzylidene)-5,5-dimethyl-3-oxopyrazolidin- 1-ium-2-ide to 2,6-disubstituted N-arylmaleimides.",
author = "Y.B. Koptelov and D.O. Antuganov and A.P. Molchanov and R.R. Kostikov",
year = "2015",
doi = "10.1134/S1070428015070143",
language = "English",
pages = "972--981",
journal = "Russian Journal of Organic Chemistry",
issn = "1070-4280",
publisher = "МАИК {"}Наука/Интерпериодика{"}",
number = "7",

}

RIS

TY - JOUR

T1 - Steric hindrances to the cycloaddition of (Z)-1-arylmethylidene-5,5-dimethyl-3-oxopyrazolidin-1-ium-2-ides to N-arylmaleimides

AU - Koptelov, Y.B.

AU - Antuganov, D.O.

AU - Molchanov, A.P.

AU - Kostikov, R.R.

PY - 2015

Y1 - 2015

N2 - © 2015 Pleiades Publishing, Ltd.Sterically hindered cycloaddition of (Z)-1-arylmethylidene-5,5-dimethyl-3-oxopyrazolidin-1-ium-2-ides to 4-mono- and 2,6-disubstituted N-arylmaleimides requires prolonged heating (40-60 h) at ~150-155°C and yields mixtures of diastereoisomeric cycloadducts. The observed diastereoselectivity is determined by both electronic and steric interactions, depending on the nature and position of substituents in the azomethine imine and maleimide. The reactions of (Z)-1-(2,6-dichlorobenzylidene)-5,5-dimethyl-3-oxopyrazolidin-1-ium-2-ide with 4-substituted N-arylmaleimides give mainly the corresponding cis adducts as a result of preferential exo attack by the dipolarophile, whereas trans adducts predominate in the cycloaddition of (Z)-1-(4-X-benzylidene)-5,5-dimethyl-3-oxopyrazolidin-1-ium-2-ide and (Z)-1-(2,6-dichlorobenzylidene)-5,5-dimethyl-3-oxopyrazolidin- 1-ium-2-ide to 2,6-disubstituted N-arylmaleimides.

AB - © 2015 Pleiades Publishing, Ltd.Sterically hindered cycloaddition of (Z)-1-arylmethylidene-5,5-dimethyl-3-oxopyrazolidin-1-ium-2-ides to 4-mono- and 2,6-disubstituted N-arylmaleimides requires prolonged heating (40-60 h) at ~150-155°C and yields mixtures of diastereoisomeric cycloadducts. The observed diastereoselectivity is determined by both electronic and steric interactions, depending on the nature and position of substituents in the azomethine imine and maleimide. The reactions of (Z)-1-(2,6-dichlorobenzylidene)-5,5-dimethyl-3-oxopyrazolidin-1-ium-2-ide with 4-substituted N-arylmaleimides give mainly the corresponding cis adducts as a result of preferential exo attack by the dipolarophile, whereas trans adducts predominate in the cycloaddition of (Z)-1-(4-X-benzylidene)-5,5-dimethyl-3-oxopyrazolidin-1-ium-2-ide and (Z)-1-(2,6-dichlorobenzylidene)-5,5-dimethyl-3-oxopyrazolidin- 1-ium-2-ide to 2,6-disubstituted N-arylmaleimides.

U2 - 10.1134/S1070428015070143

DO - 10.1134/S1070428015070143

M3 - Article

SP - 972

EP - 981

JO - Russian Journal of Organic Chemistry

JF - Russian Journal of Organic Chemistry

SN - 1070-4280

IS - 7

ER -

ID: 4004827