Facile and Diastereoselective Arylation of the Privileged 1,4-Dihydroisoquinolin-3(2H)-one Scaffold

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Facile and Diastereoselective Arylation of the Privileged 1,4-Dihydroisoquinolin-3(2H)-one Scaffold. / Дарьин, Дмитрий Викторович ; Кантин, Григорий Павлович ; Бунев, Александр Сиясатович ; Красавин, Михаил Юрьевич.

в: Beilstein Journal of Organic Chemistry, Том 18, 22.08.2022, стр. 1070–1078.

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

BibTeX

@article{148a482d52bd458faab9eada8370d46e,

title = "Facile and Diastereoselective Arylation of the Privileged 1,4-Dihydroisoquinolin-3(2H)-one Scaffold",

abstract = "A practically convenient and streamlined protocol for the trans-diastereoselective introduction of an aryl substituent at position 4 of the 1,4-dihydroisoquinol-3-one (1,4-DHIQ) scaffold is presented. The protocol involves direct Regitz diazo transfer onto readily available 3(2H)-isoquinolones followed by TfOH-promoted hydroarylation by an arene molecule. Screening of the novel 1,2,4-trisubstituted 1,4-DHIQs against cancer cell lines confirmed high cytotoxicity of selected analogs, which validates this new chemotype for further investigations as anticancer cytotoxic agents.",

keywords = "1,4-dihydroisoquinol-3-one, Regitz diazo transfer, heterocyclic diazo compounds, hydroarylation, triflic acid",

author = "Дарьин, {Дмитрий Викторович} and Кантин, {Григорий Павлович} and Бунев, {Александр Сиясатович} and Красавин, {Михаил Юрьевич}",

note = "Publisher Copyright: {\textcopyright} 2022 Dar'in et al.; licensee Beilstein-Institut.",

year = "2022",

month = aug,

day = "22",

doi = "10.3762/bjoc.18.109",

language = "English",

volume = "18",

pages = "1070–1078",

journal = "Beilstein Journal of Organic Chemistry",

issn = "1860-5397",

publisher = "Beilstein-Institut Zur Forderung der Chemischen Wissenschaften",

}

RIS

TY - JOUR

T1 - Facile and Diastereoselective Arylation of the Privileged 1,4-Dihydroisoquinolin-3(2H)-one Scaffold

AU - Дарьин, Дмитрий Викторович

AU - Кантин, Григорий Павлович

AU - Бунев, Александр Сиясатович

AU - Красавин, Михаил Юрьевич

PY - 2022/8/22

Y1 - 2022/8/22

N2 - A practically convenient and streamlined protocol for the trans-diastereoselective introduction of an aryl substituent at position 4 of the 1,4-dihydroisoquinol-3-one (1,4-DHIQ) scaffold is presented. The protocol involves direct Regitz diazo transfer onto readily available 3(2H)-isoquinolones followed by TfOH-promoted hydroarylation by an arene molecule. Screening of the novel 1,2,4-trisubstituted 1,4-DHIQs against cancer cell lines confirmed high cytotoxicity of selected analogs, which validates this new chemotype for further investigations as anticancer cytotoxic agents.

AB - A practically convenient and streamlined protocol for the trans-diastereoselective introduction of an aryl substituent at position 4 of the 1,4-dihydroisoquinol-3-one (1,4-DHIQ) scaffold is presented. The protocol involves direct Regitz diazo transfer onto readily available 3(2H)-isoquinolones followed by TfOH-promoted hydroarylation by an arene molecule. Screening of the novel 1,2,4-trisubstituted 1,4-DHIQs against cancer cell lines confirmed high cytotoxicity of selected analogs, which validates this new chemotype for further investigations as anticancer cytotoxic agents.

KW - 1,4-dihydroisoquinol-3-one

KW - Regitz diazo transfer

KW - heterocyclic diazo compounds

KW - hydroarylation

KW - triflic acid

UR - http://www.scopus.com/inward/record.url?scp=85138111589&partnerID=8YFLogxK

UR - https://www.mendeley.com/catalogue/f706da42-ed9c-391c-9a59-a610dbd73047/

U2 - 10.3762/bjoc.18.109

DO - 10.3762/bjoc.18.109

M3 - Article

C2 - 36105725

VL - 18

SP - 1070

EP - 1078

JO - Beilstein Journal of Organic Chemistry

JF - Beilstein Journal of Organic Chemistry

SN - 1860-5397

ER -

ID: 100705890