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.

In: Organic and Biomolecular Chemistry, Vol. 19, No. 27, 21.07.2021, p. 6059-6065.

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

Harvard

Касаткина, СО, Гейль, КК, Байков, СВ, Боярская, ИА & Боярский, ВП 2021, 'Catalyst-free synthesis of substituted pyridin-2-yl, quinolin-2-yl, and isoquinolin-1-yl carbamates from the corresponding hetaryl ureas and alcohols', Organic and Biomolecular Chemistry, vol. 19, no. 27, pp. 6059-6065. https://doi.org/10.1039/d1ob00783a

APA

Касаткина, С. О., Гейль, К. К., Байков, С. В., Боярская, И. А., & Боярский, В. П. (2021). Catalyst-free synthesis of substituted pyridin-2-yl, quinolin-2-yl, and isoquinolin-1-yl carbamates from the corresponding hetaryl ureas and alcohols. Organic and Biomolecular Chemistry, 19(27), 6059-6065. https://doi.org/10.1039/d1ob00783a

Vancouver

Касаткина СО, Гейль КК, Байков СВ, Боярская ИА, Боярский ВП. Catalyst-free synthesis of substituted pyridin-2-yl, quinolin-2-yl, and isoquinolin-1-yl carbamates from the corresponding hetaryl ureas and alcohols. Organic and Biomolecular Chemistry. 2021 Jul 21;19(27):6059-6065. https://doi.org/10.1039/d1ob00783a

Author

Касаткина, Светлана Олеговна ; Гейль, Кирилл Константинович ; Байков, Сергей Валентинович ; Боярская, Ирина Алексеевна ; Боярский, Вадим Павлович. / Catalyst-free synthesis of substituted pyridin-2-yl, quinolin-2-yl, and isoquinolin-1-yl carbamates from the corresponding hetaryl ureas and alcohols. In: Organic and Biomolecular Chemistry. 2021 ; Vol. 19, No. 27. pp. 6059-6065.

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