Convenient Assembly of Privileged (Hetero)Arene-Fused Benzo[1.4]oxazepines via Two Tandem SNAr Events. Part 3 – (Hetero)arene-Fused benzo[f]imidazo[1,2-d][1,4]oxazepines

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Convenient Assembly of Privileged (Hetero)Arene-Fused Benzo[1.4]oxazepines via Two Tandem S_NAr Events. Part 3 – (Hetero)arene-Fused benzo[f]imidazo[1,2-d][1,4]oxazepines. / Dmitriev, Viktor; Vedekhina, Tatiana; Sapegin, Alexander ; Krasavin, Mikhail.

In: ChemistrySelect, Vol. 5, No. 26, 15.07.2020, p. 7873-7879.

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

BibTeX

@article{e9e4cab1a9d54c22bf1c242a2acc6f65,

title = "Convenient Assembly of Privileged (Hetero)Arene-Fused Benzo[1.4]oxazepines via Two Tandem SNAr Events. Part 3 – (Hetero)arene-Fused benzo[f]imidazo[1,2-d][1,4]oxazepines",

abstract = "A tandem approach to (hetero)arene-fused benzo[f]imidazo[1,2-d][1,4]oxazepines has been described which involves condensation of bis-nucleophilic 2-(2-hydrohyaryl)imidazoles with reactivity-matched o-dihalo and o-halonitro (hetero)aromatic substrates. The process is generally regioselective with respect to the unsymmetrically substituted imidazole ring and proceeds via two SNAr events (intermolecular first and then intramolecular) intermitted by a Smiles rearrangement. In some cases, the last SNAr step provides a rare example of nucleophilic displacement of a nitro group or a halogen in non-activated positions of a (hetero)aromatic ring which does not require the use of a metal catalyst.",

keywords = "Hydroamination, nucleophilic aromatic substitution, oxygen heterocycles, privileged structures, reactivity-matched synthons, Smiles rearrangement, [1.4]oxazepines",

author = "Viktor Dmitriev and Tatiana Vedekhina and Alexander Sapegin and Mikhail Krasavin",

year = "2020",

month = jul,

day = "15",

doi = "10.1002/slct.202002033",

language = "English",

volume = "5",

pages = "7873--7879",

journal = "ChemistrySelect",

issn = "2365-6549",

publisher = "Wiley-Blackwell",

number = "26",

}

RIS

TY - JOUR

T1 - Convenient Assembly of Privileged (Hetero)Arene-Fused Benzo[1.4]oxazepines via Two Tandem SNAr Events. Part 3 – (Hetero)arene-Fused benzo[f]imidazo[1,2-d][1,4]oxazepines

AU - Dmitriev, Viktor

AU - Vedekhina, Tatiana

AU - Sapegin, Alexander

AU - Krasavin, Mikhail

PY - 2020/7/15

Y1 - 2020/7/15

N2 - A tandem approach to (hetero)arene-fused benzo[f]imidazo[1,2-d][1,4]oxazepines has been described which involves condensation of bis-nucleophilic 2-(2-hydrohyaryl)imidazoles with reactivity-matched o-dihalo and o-halonitro (hetero)aromatic substrates. The process is generally regioselective with respect to the unsymmetrically substituted imidazole ring and proceeds via two SNAr events (intermolecular first and then intramolecular) intermitted by a Smiles rearrangement. In some cases, the last SNAr step provides a rare example of nucleophilic displacement of a nitro group or a halogen in non-activated positions of a (hetero)aromatic ring which does not require the use of a metal catalyst.

AB - A tandem approach to (hetero)arene-fused benzo[f]imidazo[1,2-d][1,4]oxazepines has been described which involves condensation of bis-nucleophilic 2-(2-hydrohyaryl)imidazoles with reactivity-matched o-dihalo and o-halonitro (hetero)aromatic substrates. The process is generally regioselective with respect to the unsymmetrically substituted imidazole ring and proceeds via two SNAr events (intermolecular first and then intramolecular) intermitted by a Smiles rearrangement. In some cases, the last SNAr step provides a rare example of nucleophilic displacement of a nitro group or a halogen in non-activated positions of a (hetero)aromatic ring which does not require the use of a metal catalyst.

KW - Hydroamination

KW - nucleophilic aromatic substitution

KW - oxygen heterocycles

KW - privileged structures

KW - reactivity-matched synthons

KW - Smiles rearrangement

KW - [1.4]oxazepines

UR - http://www.scopus.com/inward/record.url?scp=85087972160&partnerID=8YFLogxK

U2 - 10.1002/slct.202002033

DO - 10.1002/slct.202002033

M3 - Article

AN - SCOPUS:85087972160

VL - 5

SP - 7873

EP - 7879

JO - ChemistrySelect

JF - ChemistrySelect

SN - 2365-6549

IS - 26

ER -

ID: 60838407