Access to 4-((Pyridin-2-yl)amino)quinazolinones via Annulation of 2-Aminobenzonitriles with N′-(Pyridin-2-yl)-N,N-dimethyl Ureas

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Access to 4-((Pyridin-2-yl)amino)quinazolinones via Annulation of 2-Aminobenzonitriles with N′-(Pyridin-2-yl)-N,N-dimethyl Ureas. / Байкова, Светлана Олеговна ; Байков, Сергей Валентинович ; Солодянкина, Ольга Владимировна ; Боярский, Вадим Павлович.

In: The Journal of organic chemistry, 21.08.2024.

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

BibTeX

@article{a3d2fa7d4dda486eb82547544531df86,

title = "Access to 4-((Pyridin-2-yl)amino)quinazolinones via Annulation of 2-Aminobenzonitriles with N′-(Pyridin-2-yl)-N,N-dimethyl Ureas",

abstract = "We have developed a convenient protocol for synthesizing N-(2-pyridyl)-substituted 4-(amino)quinazolin-2(1H)-ones by reacting N,N-dimethyl-N′-pyridylureas with 2-aminobenzonitriles. The method relies on the ability of N,N-dimethyl-N′-pyridyl/quinolinyl ureas to act as masked isocyanates under thermal activation, followed by a Dimroth rearrangement of 4-imino-3-(hetaryl)-3,4-dihydroquinazolin-2(1H)-ones. Conducted at 120 °C, either in DMF or under solvent-free conditions, this approach has produced 28 derivatives of 4-aminoquinazolinones, featuring pyridine or quinoline substituents, with yields of up to 92%.",

author = "Байкова, {Светлана Олеговна} and Байков, {Сергей Валентинович} and Солодянкина, {Ольга Владимировна} and Боярский, {Вадим Павлович}",

year = "2024",

month = aug,

day = "21",

doi = "10.1021/acs.joc.4c00974",

language = "English",

journal = "Journal of Organic Chemistry",

issn = "0022-3263",

publisher = "American Chemical Society",

}

RIS

TY - JOUR

T1 - Access to 4-((Pyridin-2-yl)amino)quinazolinones via Annulation of 2-Aminobenzonitriles with N′-(Pyridin-2-yl)-N,N-dimethyl Ureas

AU - Байкова, Светлана Олеговна

AU - Байков, Сергей Валентинович

AU - Солодянкина, Ольга Владимировна

AU - Боярский, Вадим Павлович

PY - 2024/8/21

Y1 - 2024/8/21

N2 - We have developed a convenient protocol for synthesizing N-(2-pyridyl)-substituted 4-(amino)quinazolin-2(1H)-ones by reacting N,N-dimethyl-N′-pyridylureas with 2-aminobenzonitriles. The method relies on the ability of N,N-dimethyl-N′-pyridyl/quinolinyl ureas to act as masked isocyanates under thermal activation, followed by a Dimroth rearrangement of 4-imino-3-(hetaryl)-3,4-dihydroquinazolin-2(1H)-ones. Conducted at 120 °C, either in DMF or under solvent-free conditions, this approach has produced 28 derivatives of 4-aminoquinazolinones, featuring pyridine or quinoline substituents, with yields of up to 92%.

AB - We have developed a convenient protocol for synthesizing N-(2-pyridyl)-substituted 4-(amino)quinazolin-2(1H)-ones by reacting N,N-dimethyl-N′-pyridylureas with 2-aminobenzonitriles. The method relies on the ability of N,N-dimethyl-N′-pyridyl/quinolinyl ureas to act as masked isocyanates under thermal activation, followed by a Dimroth rearrangement of 4-imino-3-(hetaryl)-3,4-dihydroquinazolin-2(1H)-ones. Conducted at 120 °C, either in DMF or under solvent-free conditions, this approach has produced 28 derivatives of 4-aminoquinazolinones, featuring pyridine or quinoline substituents, with yields of up to 92%.

UR - https://www.mendeley.com/catalogue/7dc04f3a-7754-309f-9037-6d838818cd99/

U2 - 10.1021/acs.joc.4c00974

DO - 10.1021/acs.joc.4c00974

M3 - Article

JO - Journal of Organic Chemistry

JF - Journal of Organic Chemistry

SN - 0022-3263

ER -

ID: 123004150