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Efficient Use of 1,2-Dihaloazine Synthons in Transition-Metal-Free Preparation of Doverse Heterocycle-Fused 1,4-Oxazepines. / Sapegin, A.V.; Kalinin, S.A.; Smirnov, A.V.; Dorogov, M.V.; Krasavin, M.

в: European Journal of Organic Chemistry, Том 2015, № 6, 2015, стр. 1333-1340.

Результаты исследований: Научные публикации в периодических изданиях › статья › Рецензирование

Harvard

Sapegin, AV, Kalinin, SA, Smirnov, AV, Dorogov, MV & Krasavin, M 2015, 'Efficient Use of 1,2-Dihaloazine Synthons in Transition-Metal-Free Preparation of Doverse Heterocycle-Fused 1,4-Oxazepines', European Journal of Organic Chemistry, Том. 2015, № 6, стр. 1333-1340. https://doi.org/10.1002/ejoc.201403397, https://doi.org/10.1002/ejoc.201403397, https://doi.org/10.1002/ejoc.201403397

APA

Sapegin, A. V., Kalinin, S. A., Smirnov, A. V., Dorogov, M. V., & Krasavin, M. (2015). Efficient Use of 1,2-Dihaloazine Synthons in Transition-Metal-Free Preparation of Doverse Heterocycle-Fused 1,4-Oxazepines. European Journal of Organic Chemistry, 2015(6), 1333-1340. https://doi.org/10.1002/ejoc.201403397, https://doi.org/10.1002/ejoc.201403397, https://doi.org/10.1002/ejoc.201403397

Vancouver

Sapegin AV, Kalinin SA, Smirnov AV, Dorogov MV, Krasavin M. Efficient Use of 1,2-Dihaloazine Synthons in Transition-Metal-Free Preparation of Doverse Heterocycle-Fused 1,4-Oxazepines. European Journal of Organic Chemistry. 2015;2015(6):1333-1340. https://doi.org/10.1002/ejoc.201403397, https://doi.org/10.1002/ejoc.201403397, https://doi.org/10.1002/ejoc.201403397

Author

Sapegin, A.V. ; Kalinin, S.A. ; Smirnov, A.V. ; Dorogov, M.V. ; Krasavin, M. / Efficient Use of 1,2-Dihaloazine Synthons in Transition-Metal-Free Preparation of Doverse Heterocycle-Fused 1,4-Oxazepines. в: European Journal of Organic Chemistry. 2015 ; Том 2015, № 6. стр. 1333-1340.

BibTeX

@article{4edc8e76b6ed425c8bd3485cdae9911f,
title = "Efficient Use of 1,2-Dihaloazine Synthons in Transition-Metal-Free Preparation of Doverse Heterocycle-Fused 1,4-Oxazepines",
abstract = "{\textcopyright} 2015 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim. A previously reported condensation reaction of ambiphilic 2-(1H-pyrazol-5-yl)phenols with various o-chloro-substituted nitroaromatic synthons to provide medicinally important tetracyclic pyrazolo[1,5-d][1,4]oxazepines was extended to more readily available and convenient-to-use 1,2-dihaloazines. Although 4,5-dichloropyridazin-3(2H)-ones and 2,3-dichloropyrazine are popular bis(electrophilic) partners in various SNAr-type condensations and also were efficiently used in the reaction reported herein, the facility with which various 3-bromo-2-chloropyridines underwent the same cyclization was unexpected. These reactions are presumed to occur as sequential intermolecular SNAr/Smiles rearrangement/intramolecular SNAr tandem reactions and provide a rare example of the transition-metal-free substitution of a bromine atom at the 3-position of a pyridine ring.",
author = "A.V. Sapegin and S.A. Kalinin and A.V. Smirnov and M.V. Dorogov and M. Krasavin",
year = "2015",
doi = "10.1002/ejoc.201403397",
language = "English",
volume = "2015",
pages = "1333--1340",
journal = "European Journal of Organic Chemistry",
issn = "1434-193X",
publisher = "Wiley-Blackwell",
number = "6",

}

RIS

TY - JOUR

T1 - Efficient Use of 1,2-Dihaloazine Synthons in Transition-Metal-Free Preparation of Doverse Heterocycle-Fused 1,4-Oxazepines

AU - Sapegin, A.V.

AU - Kalinin, S.A.

AU - Smirnov, A.V.

AU - Dorogov, M.V.

AU - Krasavin, M.

PY - 2015

Y1 - 2015

N2 - © 2015 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim. A previously reported condensation reaction of ambiphilic 2-(1H-pyrazol-5-yl)phenols with various o-chloro-substituted nitroaromatic synthons to provide medicinally important tetracyclic pyrazolo[1,5-d][1,4]oxazepines was extended to more readily available and convenient-to-use 1,2-dihaloazines. Although 4,5-dichloropyridazin-3(2H)-ones and 2,3-dichloropyrazine are popular bis(electrophilic) partners in various SNAr-type condensations and also were efficiently used in the reaction reported herein, the facility with which various 3-bromo-2-chloropyridines underwent the same cyclization was unexpected. These reactions are presumed to occur as sequential intermolecular SNAr/Smiles rearrangement/intramolecular SNAr tandem reactions and provide a rare example of the transition-metal-free substitution of a bromine atom at the 3-position of a pyridine ring.

AB - © 2015 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim. A previously reported condensation reaction of ambiphilic 2-(1H-pyrazol-5-yl)phenols with various o-chloro-substituted nitroaromatic synthons to provide medicinally important tetracyclic pyrazolo[1,5-d][1,4]oxazepines was extended to more readily available and convenient-to-use 1,2-dihaloazines. Although 4,5-dichloropyridazin-3(2H)-ones and 2,3-dichloropyrazine are popular bis(electrophilic) partners in various SNAr-type condensations and also were efficiently used in the reaction reported herein, the facility with which various 3-bromo-2-chloropyridines underwent the same cyclization was unexpected. These reactions are presumed to occur as sequential intermolecular SNAr/Smiles rearrangement/intramolecular SNAr tandem reactions and provide a rare example of the transition-metal-free substitution of a bromine atom at the 3-position of a pyridine ring.

U2 - 10.1002/ejoc.201403397

DO - 10.1002/ejoc.201403397

M3 - Article

VL - 2015

SP - 1333

EP - 1340

JO - European Journal of Organic Chemistry

JF - European Journal of Organic Chemistry

SN - 1434-193X

IS - 6

ER -

ID: 3924605