Convenient Assembly of Privileged (Hetero)Arene-Fused Benzo[1.4]oxazepines by Two Tandem SNAr Events. Part 2 – The Use of o-[N-(Hetero)aryl]aminomethyl Phenols

Research output

Abstract

As was anticipated based on mechanistic reasoning, bis-nucleophilic o-(arylamino)methyl phenols underwent a facile, base-promoted cyclocondensation with reactivity matched bis-electrophilic (hetero)aromatic substrates to give a rare type of substituted diarene-fused [1.4]oxazepines. This finding further supports the idea of the importance of the Smiles rearrangement in the interim of two SNAr events ultimately leading to the formation of the central cycle in the newly formed tricylic scaffold.

Original languageEnglish
JournalEuropean Journal of Organic Chemistry
DOIs
Publication statusE-pub ahead of print - 3 May 2019

Fingerprint

Oxazepines
Phenols
Scaffolds
phenols
reactivity
assembly
cycles
Substrates

Scopus subject areas

  • Physical and Theoretical Chemistry
  • Organic Chemistry

Cite this

@article{0dc9f2e7beaf4bf6998d3a34e92f4f6e,
title = "Convenient Assembly of Privileged (Hetero)Arene-Fused Benzo[1.4]oxazepines by Two Tandem SNAr Events. Part 2 – The Use of o-[N-(Hetero)aryl]aminomethyl Phenols",
abstract = "As was anticipated based on mechanistic reasoning, bis-nucleophilic o-(arylamino)methyl phenols underwent a facile, base-promoted cyclocondensation with reactivity matched bis-electrophilic (hetero)aromatic substrates to give a rare type of substituted diarene-fused [1.4]oxazepines. This finding further supports the idea of the importance of the Smiles rearrangement in the interim of two SNAr events ultimately leading to the formation of the central cycle in the newly formed tricylic scaffold.",
keywords = "Nucleophilic aromatic substitution, Privileged structures, Reactivity-matched synthons, Smiles rearrangement, [1.4]Oxazepines",
author = "Andrey Firsov and Alexander Sapegin and Mikhail Krasavin",
year = "2019",
month = "5",
day = "3",
doi = "10.1002/ejoc.201900264",
language = "English",
journal = "European Journal of Organic Chemistry",
issn = "1434-193X",
publisher = "Wiley-Blackwell",

}

TY - JOUR

T1 - Convenient Assembly of Privileged (Hetero)Arene-Fused Benzo[1.4]oxazepines by Two Tandem SNAr Events. Part 2 – The Use of o-[N-(Hetero)aryl]aminomethyl Phenols

AU - Firsov, Andrey

AU - Sapegin, Alexander

AU - Krasavin, Mikhail

PY - 2019/5/3

Y1 - 2019/5/3

N2 - As was anticipated based on mechanistic reasoning, bis-nucleophilic o-(arylamino)methyl phenols underwent a facile, base-promoted cyclocondensation with reactivity matched bis-electrophilic (hetero)aromatic substrates to give a rare type of substituted diarene-fused [1.4]oxazepines. This finding further supports the idea of the importance of the Smiles rearrangement in the interim of two SNAr events ultimately leading to the formation of the central cycle in the newly formed tricylic scaffold.

AB - As was anticipated based on mechanistic reasoning, bis-nucleophilic o-(arylamino)methyl phenols underwent a facile, base-promoted cyclocondensation with reactivity matched bis-electrophilic (hetero)aromatic substrates to give a rare type of substituted diarene-fused [1.4]oxazepines. This finding further supports the idea of the importance of the Smiles rearrangement in the interim of two SNAr events ultimately leading to the formation of the central cycle in the newly formed tricylic scaffold.

KW - Nucleophilic aromatic substitution

KW - Privileged structures

KW - Reactivity-matched synthons

KW - Smiles rearrangement

KW - [1.4]Oxazepines

UR - http://www.scopus.com/inward/record.url?scp=85066076331&partnerID=8YFLogxK

UR - http://www.mendeley.com/research/convenient-assembly-privileged-heteroarenefused-benzo14oxazepines-two-tandem-s-n-ar-events-part-2-o

U2 - 10.1002/ejoc.201900264

DO - 10.1002/ejoc.201900264

M3 - Article

AN - SCOPUS:85066076331

JO - European Journal of Organic Chemistry

JF - European Journal of Organic Chemistry

SN - 1434-193X

ER -