Convenient entry to N-pyridinylureas with pharmaceutically privileged oxadiazole substituents via the acid-catalyzed C[sbnd]H activation of N-oxides

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Convenient entry to N-pyridinylureas with pharmaceutically privileged oxadiazole substituents via the acid-catalyzed C[sbnd]H activation of N-oxides. / Geyl, Kirill ; Baykov, Sergey; Tarasenko, Marina; Zelenkov, Lev E.; Matveevskaya, Vladislava ; Boyarskiy, Vadim P.

In: Tetrahedron Letters, Vol. 60, No. 40, 151108, 03.10.2019.

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

BibTeX

@article{75cafa240a734d50b2b3584ee0000c21,

title = "Convenient entry to N-pyridinylureas with pharmaceutically privileged oxadiazole substituents via the acid-catalyzed C[sbnd]H activation of N-oxides",

abstract = "Pyridine-N-oxides bearing a pharmacophoric oxadiazole moiety could be C[sbnd]H functionalized via the acid-catalyzed reaction with dialkylcyanamides, providing access to hitherto undescribed pyridine-2-yl substituted ureas, which have potential as “lead-like” scaffolds for medicinal chemistry. Atom-economy, environmental friendliness (no halide-containing or toxic reagents), simple work-up, as well as scalability are the main advantages of the employed procedure.",

keywords = "C[sbnd]H activation, Dialkylcyanamides, N-Oxides, Ureas, Diastereoselective, Enantioselective, Tamura reaction, Organocatalysis, Vinylidene indanedione",

author = "Kirill Geyl and Sergey Baykov and Marina Tarasenko and Zelenkov, {Lev E.} and Vladislava Matveevskaya and Boyarskiy, {Vadim P.}",

note = "Publisher Copyright: {\textcopyright} 2019 Elsevier Ltd",

year = "2019",

month = oct,

day = "3",

doi = "10.1016/j.tetlet.2019.151108",

language = "English",

volume = "60",

journal = "Tetrahedron Letters",

issn = "0040-4039",

publisher = "Elsevier",

number = "40",

}

RIS

TY - JOUR

T1 - Convenient entry to N-pyridinylureas with pharmaceutically privileged oxadiazole substituents via the acid-catalyzed C[sbnd]H activation of N-oxides

AU - Geyl, Kirill

AU - Baykov, Sergey

AU - Tarasenko, Marina

AU - Zelenkov, Lev E.

AU - Matveevskaya, Vladislava

AU - Boyarskiy, Vadim P.

PY - 2019/10/3

Y1 - 2019/10/3

N2 - Pyridine-N-oxides bearing a pharmacophoric oxadiazole moiety could be C[sbnd]H functionalized via the acid-catalyzed reaction with dialkylcyanamides, providing access to hitherto undescribed pyridine-2-yl substituted ureas, which have potential as “lead-like” scaffolds for medicinal chemistry. Atom-economy, environmental friendliness (no halide-containing or toxic reagents), simple work-up, as well as scalability are the main advantages of the employed procedure.

AB - Pyridine-N-oxides bearing a pharmacophoric oxadiazole moiety could be C[sbnd]H functionalized via the acid-catalyzed reaction with dialkylcyanamides, providing access to hitherto undescribed pyridine-2-yl substituted ureas, which have potential as “lead-like” scaffolds for medicinal chemistry. Atom-economy, environmental friendliness (no halide-containing or toxic reagents), simple work-up, as well as scalability are the main advantages of the employed procedure.

KW - C[sbnd]H activation

KW - Dialkylcyanamides

KW - N-Oxides

KW - Ureas

KW - Diastereoselective

KW - Enantioselective

KW - Tamura reaction

KW - Organocatalysis

KW - Vinylidene indanedione

UR - http://www.scopus.com/inward/record.url?scp=85071979075&partnerID=8YFLogxK

U2 - 10.1016/j.tetlet.2019.151108

DO - 10.1016/j.tetlet.2019.151108

M3 - Article

AN - SCOPUS:85071979075

VL - 60

JO - Tetrahedron Letters

JF - Tetrahedron Letters

SN - 0040-4039

IS - 40

M1 - 151108

ER -

ID: 46202162