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Anthracene-fused isoxazolopyrrolo[2,1-a]isoquinolines via an endocyclic N-acyliminium ion cyclization: A joint experimental and theoretical study. / Ledovskaya, Maria S.; Molchanov, Alexander P.; Kostikov, Rafael R.; Panikorovsky, Taras L.; Gurzhiy, Vladislav V.; Ryazantsev, Mikhail N.; Boitsov, Vitali M.; Stepakov, Alexander V.

In: Tetrahedron, Vol. 72, No. 32, 2016, p. 4827-4834.

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

Harvard

Ledovskaya, MS, Molchanov, AP, Kostikov, RR, Panikorovsky, TL, Gurzhiy, VV, Ryazantsev, MN, Boitsov, VM & Stepakov, AV 2016, 'Anthracene-fused isoxazolopyrrolo[2,1-a]isoquinolines via an endocyclic N-acyliminium ion cyclization: A joint experimental and theoretical study', Tetrahedron, vol. 72, no. 32, pp. 4827-4834. https://doi.org/10.1016/j.tet.2016.06.048

APA

Ledovskaya, M. S., Molchanov, A. P., Kostikov, R. R., Panikorovsky, T. L., Gurzhiy, V. V., Ryazantsev, M. N., Boitsov, V. M., & Stepakov, A. V. (2016). Anthracene-fused isoxazolopyrrolo[2,1-a]isoquinolines via an endocyclic N-acyliminium ion cyclization: A joint experimental and theoretical study. Tetrahedron, 72(32), 4827-4834. https://doi.org/10.1016/j.tet.2016.06.048

Vancouver

Ledovskaya MS, Molchanov AP, Kostikov RR, Panikorovsky TL, Gurzhiy VV, Ryazantsev MN et al. Anthracene-fused isoxazolopyrrolo[2,1-a]isoquinolines via an endocyclic N-acyliminium ion cyclization: A joint experimental and theoretical study. Tetrahedron. 2016;72(32):4827-4834. https://doi.org/10.1016/j.tet.2016.06.048

Author

Ledovskaya, Maria S. ; Molchanov, Alexander P. ; Kostikov, Rafael R. ; Panikorovsky, Taras L. ; Gurzhiy, Vladislav V. ; Ryazantsev, Mikhail N. ; Boitsov, Vitali M. ; Stepakov, Alexander V. / Anthracene-fused isoxazolopyrrolo[2,1-a]isoquinolines via an endocyclic N-acyliminium ion cyclization: A joint experimental and theoretical study. In: Tetrahedron. 2016 ; Vol. 72, No. 32. pp. 4827-4834.

BibTeX

@article{c601a64796c948f880917ea828b3d55f,
title = "Anthracene-fused isoxazolopyrrolo[2,1-a]isoquinolines via an endocyclic N-acyliminium ion cyclization: A joint experimental and theoretical study",
abstract = "{\textcopyright} 2016 Elsevier Ltd.A simple and efficient strategy is reported for the synthesis of anthracene-fused isoxazolopyrrolo[2,1-a]isoquinolines via an endocyclic N-acyliminium ion cyclization. The cyclization of 18-aryl-21-(2-arylethyl)-22-hydroxy-16-oxa-17,21-diazahexacyclo[6.6.5.315,19.02,7.09,14.015,19]docosa-2,4,6,9,11,13,17-heptaen-20-ones proceeds with high stereoselectivity, leading to 28-aryl-30-oxa-12,29-diazaoctacyclo[13.6.6.32,14.02,14.03,12.04,9.016,21.022,27]triaconta-4,6,8,16,18,20,22,24,26,28-decaen-13-ones. The N-acyliminium cyclization of 18-aryl-21-(2-arylethyl)-20-hydroxy-16-oxa-17,21-diazahexacyclo[6.6.5.315,19.02,7.09,14.015,19]docosa-2,4,6,9,11,13,17-heptaen-22-ones occurs only for substrates with electron-rich aromatic groups in the arylalkyl fragment. In these cases, cyclization also proceeds with a high stereoselectivity with the formation of anthracene-fused isoxazolopyrrolo[2,1-a]isoquinolines as single diastereomers. To understand the mechanisms that allow for cyclization of N-acylimini",
author = "Ledovskaya, {Maria S.} and Molchanov, {Alexander P.} and Kostikov, {Rafael R.} and Panikorovsky, {Taras L.} and Gurzhiy, {Vladislav V.} and Ryazantsev, {Mikhail N.} and Boitsov, {Vitali M.} and Stepakov, {Alexander V.}",
year = "2016",
doi = "10.1016/j.tet.2016.06.048",
language = "English",
volume = "72",
pages = "4827--4834",
journal = "Tetrahedron",
issn = "0040-4020",
publisher = "Elsevier",
number = "32",

}

RIS

TY - JOUR

T1 - Anthracene-fused isoxazolopyrrolo[2,1-a]isoquinolines via an endocyclic N-acyliminium ion cyclization: A joint experimental and theoretical study

AU - Ledovskaya, Maria S.

AU - Molchanov, Alexander P.

AU - Kostikov, Rafael R.

AU - Panikorovsky, Taras L.

AU - Gurzhiy, Vladislav V.

AU - Ryazantsev, Mikhail N.

AU - Boitsov, Vitali M.

AU - Stepakov, Alexander V.

PY - 2016

Y1 - 2016

N2 - © 2016 Elsevier Ltd.A simple and efficient strategy is reported for the synthesis of anthracene-fused isoxazolopyrrolo[2,1-a]isoquinolines via an endocyclic N-acyliminium ion cyclization. The cyclization of 18-aryl-21-(2-arylethyl)-22-hydroxy-16-oxa-17,21-diazahexacyclo[6.6.5.315,19.02,7.09,14.015,19]docosa-2,4,6,9,11,13,17-heptaen-20-ones proceeds with high stereoselectivity, leading to 28-aryl-30-oxa-12,29-diazaoctacyclo[13.6.6.32,14.02,14.03,12.04,9.016,21.022,27]triaconta-4,6,8,16,18,20,22,24,26,28-decaen-13-ones. The N-acyliminium cyclization of 18-aryl-21-(2-arylethyl)-20-hydroxy-16-oxa-17,21-diazahexacyclo[6.6.5.315,19.02,7.09,14.015,19]docosa-2,4,6,9,11,13,17-heptaen-22-ones occurs only for substrates with electron-rich aromatic groups in the arylalkyl fragment. In these cases, cyclization also proceeds with a high stereoselectivity with the formation of anthracene-fused isoxazolopyrrolo[2,1-a]isoquinolines as single diastereomers. To understand the mechanisms that allow for cyclization of N-acylimini

AB - © 2016 Elsevier Ltd.A simple and efficient strategy is reported for the synthesis of anthracene-fused isoxazolopyrrolo[2,1-a]isoquinolines via an endocyclic N-acyliminium ion cyclization. The cyclization of 18-aryl-21-(2-arylethyl)-22-hydroxy-16-oxa-17,21-diazahexacyclo[6.6.5.315,19.02,7.09,14.015,19]docosa-2,4,6,9,11,13,17-heptaen-20-ones proceeds with high stereoselectivity, leading to 28-aryl-30-oxa-12,29-diazaoctacyclo[13.6.6.32,14.02,14.03,12.04,9.016,21.022,27]triaconta-4,6,8,16,18,20,22,24,26,28-decaen-13-ones. The N-acyliminium cyclization of 18-aryl-21-(2-arylethyl)-20-hydroxy-16-oxa-17,21-diazahexacyclo[6.6.5.315,19.02,7.09,14.015,19]docosa-2,4,6,9,11,13,17-heptaen-22-ones occurs only for substrates with electron-rich aromatic groups in the arylalkyl fragment. In these cases, cyclization also proceeds with a high stereoselectivity with the formation of anthracene-fused isoxazolopyrrolo[2,1-a]isoquinolines as single diastereomers. To understand the mechanisms that allow for cyclization of N-acylimini

U2 - 10.1016/j.tet.2016.06.048

DO - 10.1016/j.tet.2016.06.048

M3 - Article

VL - 72

SP - 4827

EP - 4834

JO - Tetrahedron

JF - Tetrahedron

SN - 0040-4020

IS - 32

ER -

ID: 7596274