Catalyst-free synthesis of substituted pyridin-2-yl, quinolin-2-yl, and isoquinolin-1-yl carbamates from the corresponding hetaryl ureas and alcohols

Standard

Catalyst-free synthesis of substituted pyridin-2-yl, quinolin-2-yl, and isoquinolin-1-yl carbamates from the corresponding hetaryl ureas and alcohols. / Касаткина, Светлана Олеговна ; Гейль, Кирилл Константинович ; Байков, Сергей Валентинович ; Боярская, Ирина Алексеевна ; Боярский, Вадим Павлович.

в: Organic and Biomolecular Chemistry, Том 19, № 27, 21.07.2021, стр. 6059-6065.

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

BibTeX

@article{e64cc438cf834171aa2e42d8f8df876e,

title = "Catalyst-free synthesis of substituted pyridin-2-yl, quinolin-2-yl, and isoquinolin-1-yl carbamates from the corresponding hetaryl ureas and alcohols",

abstract = "A novel catalyst-free synthesis ofN-pyridin-2-yl,N-quinolin-2-yl, andN-isoquinolin-1-yl carbamates utilizes easily accessibleN-hetaryl ureas and alcohols. The proposed environmentally friendly technique is suitable for the good-to-high yielding synthesis of a wide range ofN-pyridin-2-yl orN-quinolin-2-yl substituted carbamates featuring electron-donating and electron-withdrawing groups in the azine rings and containing various primary, secondary, and even tertiary alkyl substituents at the oxygen atom (48-94%; 31 examples). The DFT calculation and experimental study showed that the reaction proceeds through the intermediate formation of hetaryl isocyanates. The method can be applied to obtainN-isoquinolin-1-yl carbamates, although in lower yields, and ethyl benzo[h]quinolin-2-yl carbamate has also been successfully synthesized (68%).",

keywords = "1,6-DIENES, AMINES, CARBONATES, CHEMISTRY, CO2, DISCOVERY, ENCAPSULATION, INHIBITORS, MONOMERS, ONE-POT SYNTHESIS",

author = "Касаткина, {Светлана Олеговна} and Гейль, {Кирилл Константинович} and Байков, {Сергей Валентинович} and Боярская, {Ирина Алексеевна} and Боярский, {Вадим Павлович}",

note = "Publisher Copyright: {\textcopyright} The Royal Society of Chemistry 2021.",

year = "2021",

month = jul,

day = "21",

doi = "10.1039/d1ob00783a",

language = "English",

volume = "19",

pages = "6059--6065",

journal = "Organic and Biomolecular Chemistry",

issn = "1477-0520",

publisher = "Royal Society of Chemistry",

number = "27",

}

RIS

TY - JOUR

T1 - Catalyst-free synthesis of substituted pyridin-2-yl, quinolin-2-yl, and isoquinolin-1-yl carbamates from the corresponding hetaryl ureas and alcohols

AU - Касаткина, Светлана Олеговна

AU - Гейль, Кирилл Константинович

AU - Байков, Сергей Валентинович

AU - Боярская, Ирина Алексеевна

AU - Боярский, Вадим Павлович

N1 - Publisher Copyright: © The Royal Society of Chemistry 2021.

PY - 2021/7/21

Y1 - 2021/7/21

N2 - A novel catalyst-free synthesis ofN-pyridin-2-yl,N-quinolin-2-yl, andN-isoquinolin-1-yl carbamates utilizes easily accessibleN-hetaryl ureas and alcohols. The proposed environmentally friendly technique is suitable for the good-to-high yielding synthesis of a wide range ofN-pyridin-2-yl orN-quinolin-2-yl substituted carbamates featuring electron-donating and electron-withdrawing groups in the azine rings and containing various primary, secondary, and even tertiary alkyl substituents at the oxygen atom (48-94%; 31 examples). The DFT calculation and experimental study showed that the reaction proceeds through the intermediate formation of hetaryl isocyanates. The method can be applied to obtainN-isoquinolin-1-yl carbamates, although in lower yields, and ethyl benzo[h]quinolin-2-yl carbamate has also been successfully synthesized (68%).

AB - A novel catalyst-free synthesis ofN-pyridin-2-yl,N-quinolin-2-yl, andN-isoquinolin-1-yl carbamates utilizes easily accessibleN-hetaryl ureas and alcohols. The proposed environmentally friendly technique is suitable for the good-to-high yielding synthesis of a wide range ofN-pyridin-2-yl orN-quinolin-2-yl substituted carbamates featuring electron-donating and electron-withdrawing groups in the azine rings and containing various primary, secondary, and even tertiary alkyl substituents at the oxygen atom (48-94%; 31 examples). The DFT calculation and experimental study showed that the reaction proceeds through the intermediate formation of hetaryl isocyanates. The method can be applied to obtainN-isoquinolin-1-yl carbamates, although in lower yields, and ethyl benzo[h]quinolin-2-yl carbamate has also been successfully synthesized (68%).

KW - 1,6-DIENES

KW - AMINES

KW - CARBONATES

KW - CHEMISTRY

KW - CO2

KW - DISCOVERY

KW - ENCAPSULATION

KW - INHIBITORS

KW - MONOMERS

KW - ONE-POT SYNTHESIS

UR - http://www.scopus.com/inward/record.url?scp=85110342880&partnerID=8YFLogxK

UR - https://www.mendeley.com/catalogue/f28756ab-2639-3922-bbf8-c33ab2aaaed3/

U2 - 10.1039/d1ob00783a

DO - 10.1039/d1ob00783a

M3 - Article

VL - 19

SP - 6059

EP - 6065

JO - Organic and Biomolecular Chemistry

JF - Organic and Biomolecular Chemistry

SN - 1477-0520

IS - 27

ER -

ID: 78908560