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Zinc(II)-mediated generation of 5-amino substituted 2,3-dihydro-1,2,4-oxadiazoles and their further ZnII-catalyzed and O2-involving transformations. / Smirnov, Andrey S.; Yandanova, Ekaterina S.; Bokach, Nadezhda A.; Starova, Galina L.; Gurzhiy, Vladislav V.; Avdontceva, Margarita S.; Zolotarev, Andrey A.; Kukushkin, Vadim Yu.

In: New Journal of Chemistry, Vol. 39, No. 12, 2015, p. 9330–9344.

Research output: Contribution to journal › Article

Harvard

Smirnov, AS, Yandanova, ES, Bokach, NA, Starova, GL, Gurzhiy, VV, Avdontceva, MS, Zolotarev, AA & Kukushkin, VY 2015, 'Zinc(II)-mediated generation of 5-amino substituted 2,3-dihydro-1,2,4-oxadiazoles and their further ZnII-catalyzed and O2-involving transformations', New Journal of Chemistry, vol. 39, no. 12, pp. 9330–9344. https://doi.org/10.1039/c5nj02061a

APA

Smirnov, A. S., Yandanova, E. S., Bokach, N. A., Starova, G. L., Gurzhiy, V. V., Avdontceva, M. S., Zolotarev, A. A., & Kukushkin, V. Y. (2015). Zinc(II)-mediated generation of 5-amino substituted 2,3-dihydro-1,2,4-oxadiazoles and their further ZnII-catalyzed and O2-involving transformations. New Journal of Chemistry, 39(12), 9330–9344. https://doi.org/10.1039/c5nj02061a

Vancouver

Smirnov AS, Yandanova ES, Bokach NA, Starova GL, Gurzhiy VV, Avdontceva MS et al. Zinc(II)-mediated generation of 5-amino substituted 2,3-dihydro-1,2,4-oxadiazoles and their further ZnII-catalyzed and O2-involving transformations. New Journal of Chemistry. 2015;39(12):9330–9344. https://doi.org/10.1039/c5nj02061a

Author

Smirnov, Andrey S. ; Yandanova, Ekaterina S. ; Bokach, Nadezhda A. ; Starova, Galina L. ; Gurzhiy, Vladislav V. ; Avdontceva, Margarita S. ; Zolotarev, Andrey A. ; Kukushkin, Vadim Yu. / Zinc(II)-mediated generation of 5-amino substituted 2,3-dihydro-1,2,4-oxadiazoles and their further ZnII-catalyzed and O2-involving transformations. In: New Journal of Chemistry. 2015 ; Vol. 39, No. 12. pp. 9330–9344.

BibTeX

@article{ee33fbb1aae24770806b9bfcb9c8dd11,
title = "Zinc(II)-mediated generation of 5-amino substituted 2,3-dihydro-1,2,4-oxadiazoles and their further ZnII-catalyzed and O2-involving transformations",
abstract = "ZnII-activated cyanamides NCNR2 (R2 = Me2, Et2, C5H10, (CH2)2O(CH2)2, Ph2) react with the acyclic N-alkyl ketonitrones Ph2CQN+ (O)R0 (R0 = Me, CH2Ph) and N-aryl ketonitrones (R0 = Ph, p-BrC6H4, p-EtC6H4) under mild conditions. Uncomplexed 5-aminosubstituted 2,3-dihydro-1,2,4-oxadiazoles (6 examples; 49–82%) were obtained in zinc(II)-involving cycloaddition of the N-alkyl ketonitrones to the cyanamide substrates; these 2,3-dihydro-1,2,4-oxadiazoles undergo ring-opening giving carbamoylamidines and methylidenureas. The N-aryl ketonitrones react with ZnII-activated cyanamides giving the open-chain systems, viz. carbamoylamidines, N0 -(2-(diphenylmethylidene)amino)-phenyl-N,N-carbamimidic acids, and methylidenureas, which are presumably formed via the cycloaddition route followed by the N–O cleavage induced by the acceptor character of the aryl groups.",
author = "Smirnov, {Andrey S.} and Yandanova, {Ekaterina S.} and Bokach, {Nadezhda A.} and Starova, {Galina L.} and Gurzhiy, {Vladislav V.} and Avdontceva, {Margarita S.} and Zolotarev, {Andrey A.} and Kukushkin, {Vadim Yu.}",
year = "2015",
doi = "10.1039/c5nj02061a",
language = "English",
volume = "39",
pages = "9330–9344",
journal = "New Journal of Chemistry",
issn = "1144-0546",
publisher = "Royal Society of Chemistry",
number = "12",

}

RIS

TY - JOUR

T1 - Zinc(II)-mediated generation of 5-amino substituted 2,3-dihydro-1,2,4-oxadiazoles and their further ZnII-catalyzed and O2-involving transformations

AU - Smirnov, Andrey S.

AU - Yandanova, Ekaterina S.

AU - Bokach, Nadezhda A.

AU - Starova, Galina L.

AU - Gurzhiy, Vladislav V.

AU - Avdontceva, Margarita S.

AU - Zolotarev, Andrey A.

AU - Kukushkin, Vadim Yu.

PY - 2015

Y1 - 2015

N2 - ZnII-activated cyanamides NCNR2 (R2 = Me2, Et2, C5H10, (CH2)2O(CH2)2, Ph2) react with the acyclic N-alkyl ketonitrones Ph2CQN+ (O)R0 (R0 = Me, CH2Ph) and N-aryl ketonitrones (R0 = Ph, p-BrC6H4, p-EtC6H4) under mild conditions. Uncomplexed 5-aminosubstituted 2,3-dihydro-1,2,4-oxadiazoles (6 examples; 49–82%) were obtained in zinc(II)-involving cycloaddition of the N-alkyl ketonitrones to the cyanamide substrates; these 2,3-dihydro-1,2,4-oxadiazoles undergo ring-opening giving carbamoylamidines and methylidenureas. The N-aryl ketonitrones react with ZnII-activated cyanamides giving the open-chain systems, viz. carbamoylamidines, N0 -(2-(diphenylmethylidene)amino)-phenyl-N,N-carbamimidic acids, and methylidenureas, which are presumably formed via the cycloaddition route followed by the N–O cleavage induced by the acceptor character of the aryl groups.

AB - ZnII-activated cyanamides NCNR2 (R2 = Me2, Et2, C5H10, (CH2)2O(CH2)2, Ph2) react with the acyclic N-alkyl ketonitrones Ph2CQN+ (O)R0 (R0 = Me, CH2Ph) and N-aryl ketonitrones (R0 = Ph, p-BrC6H4, p-EtC6H4) under mild conditions. Uncomplexed 5-aminosubstituted 2,3-dihydro-1,2,4-oxadiazoles (6 examples; 49–82%) were obtained in zinc(II)-involving cycloaddition of the N-alkyl ketonitrones to the cyanamide substrates; these 2,3-dihydro-1,2,4-oxadiazoles undergo ring-opening giving carbamoylamidines and methylidenureas. The N-aryl ketonitrones react with ZnII-activated cyanamides giving the open-chain systems, viz. carbamoylamidines, N0 -(2-(diphenylmethylidene)amino)-phenyl-N,N-carbamimidic acids, and methylidenureas, which are presumably formed via the cycloaddition route followed by the N–O cleavage induced by the acceptor character of the aryl groups.

U2 - 10.1039/c5nj02061a

DO - 10.1039/c5nj02061a

M3 - Article

VL - 39

SP - 9330

EP - 9344

JO - New Journal of Chemistry

JF - New Journal of Chemistry

SN - 1144-0546

IS - 12

ER -

ID: 3946411