Standard

Acid-catalyzed rearrangement of 1-acyl-2-azabuta-1,3-dienes to 4-pyrrolin-2-ones. / Rostovskii, Nikolai V.; Smetanin, Ilia A.; Koronatov, Alexander N.; Agafonova, Anastasiya V.; Potapenkov, Vasilii V.; Khlebnikov, Alexander F.; Novikov, Mikhail S.

In: Chemistry of Heterocyclic Compounds, Vol. 56, No. 7, 07.2020, p. 881-887.

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

Harvard

Rostovskii, NV, Smetanin, IA, Koronatov, AN, Agafonova, AV, Potapenkov, VV, Khlebnikov, AF & Novikov, MS 2020, 'Acid-catalyzed rearrangement of 1-acyl-2-azabuta-1,3-dienes to 4-pyrrolin-2-ones', Chemistry of Heterocyclic Compounds, vol. 56, no. 7, pp. 881-887. https://doi.org/10.1007/s10593-020-02745-x

APA

Rostovskii, N. V., Smetanin, I. A., Koronatov, A. N., Agafonova, A. V., Potapenkov, V. V., Khlebnikov, A. F., & Novikov, M. S. (2020). Acid-catalyzed rearrangement of 1-acyl-2-azabuta-1,3-dienes to 4-pyrrolin-2-ones. Chemistry of Heterocyclic Compounds, 56(7), 881-887. https://doi.org/10.1007/s10593-020-02745-x

Vancouver

Rostovskii NV, Smetanin IA, Koronatov AN, Agafonova AV, Potapenkov VV, Khlebnikov AF et al. Acid-catalyzed rearrangement of 1-acyl-2-azabuta-1,3-dienes to 4-pyrrolin-2-ones. Chemistry of Heterocyclic Compounds. 2020 Jul;56(7):881-887. https://doi.org/10.1007/s10593-020-02745-x

Author

Rostovskii, Nikolai V. ; Smetanin, Ilia A. ; Koronatov, Alexander N. ; Agafonova, Anastasiya V. ; Potapenkov, Vasilii V. ; Khlebnikov, Alexander F. ; Novikov, Mikhail S. / Acid-catalyzed rearrangement of 1-acyl-2-azabuta-1,3-dienes to 4-pyrrolin-2-ones. In: Chemistry of Heterocyclic Compounds. 2020 ; Vol. 56, No. 7. pp. 881-887.

BibTeX

@article{5255f9dcd6ec4ca6a6d26e6e183804d1,
title = "Acid-catalyzed rearrangement of 1-acyl-2-azabuta-1,3-dienes to 4-pyrrolin-2-ones",
abstract = "[Figure not available: see fulltext.] 1-Acyl-2-azabuta-1,3-dienes underwent rearrangement to 4-pyrrolin-2-ones in the presence of acidic catalysts (silica gel or ZnCl2) and water. The reaction proceeded via the formation of 2,3-dihydroxy-3,4-dihydropyrrole and 2-hydroxy-2Н-pyrrole intermediates, the latter of which was transformed by [1,5]-sigmatropic shift of carbonyl substituent and prototropic isomerization. 4-Chloro-substituted 1-acetyl-2-azabuta-1,3-dienes were stable toward rearrangement, while brominated analogs rearranged into 4-pyrrolin-2-ones, probably as a result of the initial radical hydrodebromination. According to calculations performed at the DFT level, two steps of the reaction were catalyzed by acid: the cyclization of 2-azabutadiene and the sigmatropic shift in the 2-hydroxy-2Н-pyrrole intermediate.",
keywords = "acid catalysis, azabuta-1,3-dienes, pyrrolinones, sigmatropic shift",
author = "Rostovskii, {Nikolai V.} and Smetanin, {Ilia A.} and Koronatov, {Alexander N.} and Agafonova, {Anastasiya V.} and Potapenkov, {Vasilii V.} and Khlebnikov, {Alexander F.} and Novikov, {Mikhail S.}",
note = "Rostovskii, N.V., Smetanin, I.A., Koronatov, A.N. et al. Acid-catalyzed rearrangement of 1-acyl-2-azabuta-1,3-dienes to 4-pyrrolin-2-ones. Chem Heterocycl Comp 56, 881–887 (2020). https://doi.org/10.1007/s10593-020-02745-x",
year = "2020",
month = jul,
doi = "10.1007/s10593-020-02745-x",
language = "English",
volume = "56",
pages = "881--887",
journal = "Chemistry of Heterocyclic Compounds",
issn = "0009-3122",
publisher = "Springer Nature",
number = "7",

}

RIS

TY - JOUR

T1 - Acid-catalyzed rearrangement of 1-acyl-2-azabuta-1,3-dienes to 4-pyrrolin-2-ones

AU - Rostovskii, Nikolai V.

AU - Smetanin, Ilia A.

AU - Koronatov, Alexander N.

AU - Agafonova, Anastasiya V.

AU - Potapenkov, Vasilii V.

AU - Khlebnikov, Alexander F.

AU - Novikov, Mikhail S.

N1 - Rostovskii, N.V., Smetanin, I.A., Koronatov, A.N. et al. Acid-catalyzed rearrangement of 1-acyl-2-azabuta-1,3-dienes to 4-pyrrolin-2-ones. Chem Heterocycl Comp 56, 881–887 (2020). https://doi.org/10.1007/s10593-020-02745-x

PY - 2020/7

Y1 - 2020/7

N2 - [Figure not available: see fulltext.] 1-Acyl-2-azabuta-1,3-dienes underwent rearrangement to 4-pyrrolin-2-ones in the presence of acidic catalysts (silica gel or ZnCl2) and water. The reaction proceeded via the formation of 2,3-dihydroxy-3,4-dihydropyrrole and 2-hydroxy-2Н-pyrrole intermediates, the latter of which was transformed by [1,5]-sigmatropic shift of carbonyl substituent and prototropic isomerization. 4-Chloro-substituted 1-acetyl-2-azabuta-1,3-dienes were stable toward rearrangement, while brominated analogs rearranged into 4-pyrrolin-2-ones, probably as a result of the initial radical hydrodebromination. According to calculations performed at the DFT level, two steps of the reaction were catalyzed by acid: the cyclization of 2-azabutadiene and the sigmatropic shift in the 2-hydroxy-2Н-pyrrole intermediate.

AB - [Figure not available: see fulltext.] 1-Acyl-2-azabuta-1,3-dienes underwent rearrangement to 4-pyrrolin-2-ones in the presence of acidic catalysts (silica gel or ZnCl2) and water. The reaction proceeded via the formation of 2,3-dihydroxy-3,4-dihydropyrrole and 2-hydroxy-2Н-pyrrole intermediates, the latter of which was transformed by [1,5]-sigmatropic shift of carbonyl substituent and prototropic isomerization. 4-Chloro-substituted 1-acetyl-2-azabuta-1,3-dienes were stable toward rearrangement, while brominated analogs rearranged into 4-pyrrolin-2-ones, probably as a result of the initial radical hydrodebromination. According to calculations performed at the DFT level, two steps of the reaction were catalyzed by acid: the cyclization of 2-azabutadiene and the sigmatropic shift in the 2-hydroxy-2Н-pyrrole intermediate.

KW - acid catalysis

KW - azabuta-1,3-dienes

KW - pyrrolinones

KW - sigmatropic shift

UR - http://www.scopus.com/inward/record.url?scp=85089871074&partnerID=8YFLogxK

UR - https://www.mendeley.com/catalogue/33ec9d45-5403-33a5-9ee6-9b351a59b3a3/

U2 - 10.1007/s10593-020-02745-x

DO - 10.1007/s10593-020-02745-x

M3 - Article

AN - SCOPUS:85089871074

VL - 56

SP - 881

EP - 887

JO - Chemistry of Heterocyclic Compounds

JF - Chemistry of Heterocyclic Compounds

SN - 0009-3122

IS - 7

ER -

ID: 62041699