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

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Convenient Assembly of Privileged (Hetero)Arene-Fused Benzo[1.4]oxazepines by Two Tandem S_NAr Events. Part 2 – The Use of o-[N-(Hetero)aryl]aminomethyl Phenols. / Firsov, Andrey ; Sapegin, Alexander ; Krasavin, Mikhail.

In: European Journal of Organic Chemistry, Vol. 2019, No. 31-32, 2019, p. 5242-5246.

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

BibTeX

@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, [1, STRATEGY, CONSTRUCTION, 4]Oxazepines",

author = "Andrey Firsov and Alexander Sapegin and Mikhail Krasavin",

note = "Publisher Copyright: {\textcopyright} 2019 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim",

year = "2019",

doi = "10.1002/ejoc.201900264",

language = "English",

volume = "2019",

pages = "5242--5246",

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 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

Y1 - 2019

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

KW - [1

KW - STRATEGY

KW - CONSTRUCTION

KW - 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

VL - 2019

SP - 5242

EP - 5246

JO - European Journal of Organic Chemistry

JF - European Journal of Organic Chemistry

SN - 1434-193X

IS - 31-32

ER -

ID: 42615331