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Convenient Assembly of Privileged (Hetero)Arene-Fused Benzo[1.4]oxazepines via Two Tandem S N Ar Events. Part 1 – On the Importance of the Intermittent Smiles Rearrangement. / Sapegin, Alexander; Krasavin, Mikhail.

в: European Journal of Organic Chemistry, Том 2019, № 31-32, 2019, стр. 5234-5241.

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

Harvard

Sapegin, A & Krasavin, M 2019, 'Convenient Assembly of Privileged (Hetero)Arene-Fused Benzo[1.4]oxazepines via Two Tandem S N Ar Events. Part 1 – On the Importance of the Intermittent Smiles Rearrangement', European Journal of Organic Chemistry, Том. 2019, № 31-32, стр. 5234-5241. https://doi.org/10.1002/ejoc.201900263

APA

Sapegin, A., & Krasavin, M. (2019). Convenient Assembly of Privileged (Hetero)Arene-Fused Benzo[1.4]oxazepines via Two Tandem S N Ar Events. Part 1 – On the Importance of the Intermittent Smiles Rearrangement. European Journal of Organic Chemistry, 2019(31-32), 5234-5241. https://doi.org/10.1002/ejoc.201900263

Vancouver

Sapegin A, Krasavin M. Convenient Assembly of Privileged (Hetero)Arene-Fused Benzo[1.4]oxazepines via Two Tandem S N Ar Events. Part 1 – On the Importance of the Intermittent Smiles Rearrangement. European Journal of Organic Chemistry. 2019;2019(31-32):5234-5241. https://doi.org/10.1002/ejoc.201900263

Author

Sapegin, Alexander ; Krasavin, Mikhail. / Convenient Assembly of Privileged (Hetero)Arene-Fused Benzo[1.4]oxazepines via Two Tandem S N Ar Events. Part 1 – On the Importance of the Intermittent Smiles Rearrangement. в: European Journal of Organic Chemistry. 2019 ; Том 2019, № 31-32. стр. 5234-5241.

BibTeX

@article{fb8346ae2d8644cca9e00221e3e86935,
title = "Convenient Assembly of Privileged (Hetero)Arene-Fused Benzo[1.4]oxazepines via Two Tandem S N Ar Events. Part 1 – On the Importance of the Intermittent Smiles Rearrangement",
abstract = " New bis-nucleophilic precursors to [1.4]oxazepines synthesized via S N Ar-Smiles rearrangement-S N Ar cascade have been designed. Employing them in base-promoted condensation with aromatic bis-electrophiles allowed differentiating between highly and poorly reactive substrates (i.e. those which can and cannot pass through the Smiles rearrangement barrier, respectively). The reactivity toward the desired course of cyclization can be restored by introducing electron-withdrawing substituents in the bis-electrophile precursor. This strongly argues for the importance of the Smiles rearrangement for the successful overall ring formation. ",
keywords = "Nucleophilic aromatic substitution, Oxazepines, Privileged structures, Smiles rearrangement, Synthons, STRATEGY, CONSTRUCTION, DISCOVERY",
author = "Alexander Sapegin and Mikhail Krasavin",
note = "Publisher Copyright: {\textcopyright} 2019 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim",
year = "2019",
doi = "10.1002/ejoc.201900263",
language = "English",
volume = "2019",
pages = "5234--5241",
journal = "European Journal of Organic Chemistry",
issn = "1434-193X",
publisher = "Wiley-Blackwell",
number = "31-32",

}

RIS

TY - JOUR

T1 - Convenient Assembly of Privileged (Hetero)Arene-Fused Benzo[1.4]oxazepines via Two Tandem S N Ar Events. Part 1 – On the Importance of the Intermittent Smiles Rearrangement

AU - Sapegin, Alexander

AU - Krasavin, Mikhail

N1 - Publisher Copyright: © 2019 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim

PY - 2019

Y1 - 2019

N2 - New bis-nucleophilic precursors to [1.4]oxazepines synthesized via S N Ar-Smiles rearrangement-S N Ar cascade have been designed. Employing them in base-promoted condensation with aromatic bis-electrophiles allowed differentiating between highly and poorly reactive substrates (i.e. those which can and cannot pass through the Smiles rearrangement barrier, respectively). The reactivity toward the desired course of cyclization can be restored by introducing electron-withdrawing substituents in the bis-electrophile precursor. This strongly argues for the importance of the Smiles rearrangement for the successful overall ring formation.

AB - New bis-nucleophilic precursors to [1.4]oxazepines synthesized via S N Ar-Smiles rearrangement-S N Ar cascade have been designed. Employing them in base-promoted condensation with aromatic bis-electrophiles allowed differentiating between highly and poorly reactive substrates (i.e. those which can and cannot pass through the Smiles rearrangement barrier, respectively). The reactivity toward the desired course of cyclization can be restored by introducing electron-withdrawing substituents in the bis-electrophile precursor. This strongly argues for the importance of the Smiles rearrangement for the successful overall ring formation.

KW - Nucleophilic aromatic substitution

KW - Oxazepines

KW - Privileged structures

KW - Smiles rearrangement

KW - Synthons

KW - STRATEGY

KW - CONSTRUCTION

KW - DISCOVERY

UR - http://www.scopus.com/inward/record.url?scp=85065096071&partnerID=8YFLogxK

UR - http://www.mendeley.com/research/convenient-assembly-privileged-heteroarenefused-benzo14oxazepines-via-two-tandem-s-n-ar-events-part

U2 - 10.1002/ejoc.201900263

DO - 10.1002/ejoc.201900263

M3 - Article

AN - SCOPUS:85065096071

VL - 2019

SP - 5234

EP - 5241

JO - European Journal of Organic Chemistry

JF - European Journal of Organic Chemistry

SN - 1434-193X

IS - 31-32

ER -

ID: 41782260