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

Research outputpeer-review

Abstract

Pyridine-N-oxides bearing a pharmacophoric oxadiazole moiety could be CH 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.
Original languageEnglish
Article number151108
Number of pages4
JournalTetrahedron Letters
Volume60
Issue number40
Early online date4 Sep 2019
Publication statusPublished - 3 Oct 2019

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Bearings (structural)
Oxadiazoles
Pharmaceutical Chemistry
Poisons
Scaffolds
Oxides
Urea
Scalability
Chemical activation
Atoms
Acids
pyridine
pyridine N-oxide
Lead

Cite this

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abstract = "Pyridine-N-oxides bearing a pharmacophoric oxadiazole moiety could be CH 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.",
author = "Kirill Geyl and Sergey Baykov and Marina Tarasenko and Zelenkov, {Lev E.} and Vladislava Matveevskaya and Boyarskiy, {Vadim P.}",
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T1 - Convenient entry to N-pyridinylureas with pharmaceutically privileged oxadiazole substituents via the acid-catalyzed C 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 CH 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 CH 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.

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JO - Tetrahedron Letters

JF - Tetrahedron Letters

SN - 0040-4039

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