“Urea to Urea” Approach: Access to Unsymmetrical Ureas Bearing Pyridyl Substituents

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“Urea to Urea” Approach: Access to Unsymmetrical Ureas Bearing Pyridyl Substituents. / Касаткина, Светлана Олеговна; Гейль, Кирилл Константинович ; Байков, Сергей Валентинович ; Новиков, Михаил Сергеевич ; Боярский, Вадим Павлович.

In: Advanced Synthesis and Catalysis, Vol. 364, No. 7, 30.03.2022, p. 1295-1304.

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

BibTeX

@article{ede9cb1438114ee2857158229e2825ea,

title = "“Urea to Urea” Approach: Access to Unsymmetrical Ureas Bearing Pyridyl Substituents",

abstract = "A protocol for the synthesis of unsymmetrical ureas substituted by pyridyl/quinolinyl moiety has been developed. This method concluded in metal- and base-free reamination of N,N-dimethyl-N{\textquoteleft}-hetaryl ureas with a wide range of aryl and alkyl amines. The isolated yields vary from 40 to 96% depending on the nucleophilicity of the amines. The scope of this method includes more than 50 examples. The reaction is not hindered by either donor or acceptor groups as well as diverse functionalities. The synthesis can be easily scaled to gram quantities. Theoretical calculations supported by experimental data allowed us to propose a plausible mechanism for the process. This reaction takes place through the intermediate formation of hetaryl isocyanate.",

keywords = "Amines; Heterocycles, Masked hetaryl isocyanates, Metal-free synthesis, N-hetaryl ureas, Heterocycles, CATALYZED CARBONYLATION, Amines, DISCOVERY, BLOCKED ISOCYANATES, AMINES, BIOLOGICAL EVALUATION, GLUCOKINASE ACTIVATORS, DERIVATIVES, MASKED ISOCYANATES FACILE, PARALLEL SYNTHESIS, ANION-BINDING",

author = "Касаткина, {Светлана Олеговна} and Гейль, {Кирилл Константинович} and Байков, {Сергей Валентинович} and Новиков, {Михаил Сергеевич} and Боярский, {Вадим Павлович}",

note = "Publisher Copyright: {\textcopyright} 2022 Wiley-VCH GmbH",

year = "2022",

month = mar,

day = "30",

doi = "10.1002/adsc.202101490",

language = "English",

volume = "364",

pages = "1295--1304",

journal = "Advanced Synthesis and Catalysis",

issn = "1615-4150",

publisher = "Wiley-Blackwell",

number = "7",

}

RIS

TY - JOUR

T1 - “Urea to Urea” Approach: Access to Unsymmetrical Ureas Bearing Pyridyl Substituents

AU - Касаткина, Светлана Олеговна

AU - Гейль, Кирилл Константинович

AU - Байков, Сергей Валентинович

AU - Новиков, Михаил Сергеевич

AU - Боярский, Вадим Павлович

PY - 2022/3/30

Y1 - 2022/3/30

N2 - A protocol for the synthesis of unsymmetrical ureas substituted by pyridyl/quinolinyl moiety has been developed. This method concluded in metal- and base-free reamination of N,N-dimethyl-N‘-hetaryl ureas with a wide range of aryl and alkyl amines. The isolated yields vary from 40 to 96% depending on the nucleophilicity of the amines. The scope of this method includes more than 50 examples. The reaction is not hindered by either donor or acceptor groups as well as diverse functionalities. The synthesis can be easily scaled to gram quantities. Theoretical calculations supported by experimental data allowed us to propose a plausible mechanism for the process. This reaction takes place through the intermediate formation of hetaryl isocyanate.

AB - A protocol for the synthesis of unsymmetrical ureas substituted by pyridyl/quinolinyl moiety has been developed. This method concluded in metal- and base-free reamination of N,N-dimethyl-N‘-hetaryl ureas with a wide range of aryl and alkyl amines. The isolated yields vary from 40 to 96% depending on the nucleophilicity of the amines. The scope of this method includes more than 50 examples. The reaction is not hindered by either donor or acceptor groups as well as diverse functionalities. The synthesis can be easily scaled to gram quantities. Theoretical calculations supported by experimental data allowed us to propose a plausible mechanism for the process. This reaction takes place through the intermediate formation of hetaryl isocyanate.

KW - Amines; Heterocycles

KW - Masked hetaryl isocyanates

KW - Metal-free synthesis

KW - N-hetaryl ureas

KW - Heterocycles

KW - CATALYZED CARBONYLATION

KW - Amines

KW - DISCOVERY

KW - BLOCKED ISOCYANATES

KW - AMINES

KW - BIOLOGICAL EVALUATION

KW - GLUCOKINASE ACTIVATORS

KW - DERIVATIVES

KW - MASKED ISOCYANATES FACILE

KW - PARALLEL SYNTHESIS

KW - ANION-BINDING

UR - http://www.scopus.com/inward/record.url?scp=85126045687&partnerID=8YFLogxK

UR - https://www.mendeley.com/catalogue/e51e22f8-9c3d-376d-aab6-f9a5e991650f/

U2 - 10.1002/adsc.202101490

DO - 10.1002/adsc.202101490

M3 - Article

VL - 364

SP - 1295

EP - 1304

JO - Advanced Synthesis and Catalysis

JF - Advanced Synthesis and Catalysis

SN - 1615-4150

IS - 7

ER -

ID: 93324234