Synthesis 2019; 51(02): 414-420
© Georg Thieme Verlag Stuttgart · New York
Practical Deoxygenation of Oxazole N -Oxides by PCl3 /Collidine
Valerii Z. Shirinian*
a
N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, 47 Leninsky prosp., 119991 Moscow, Russian Federation
,
Ilya A. Lonshakov
b
Mendeleev University of Chemical Technology of Russia, Miusskaya Sq. 9, 125047 Moscow, Russian Federation Email:
shir@ioc.ac.ru
,
Alexey V. Zakharov
a
N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, 47 Leninsky prosp., 119991 Moscow, Russian Federation
,
Andrey G. Lvov
a
N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, 47 Leninsky prosp., 119991 Moscow, Russian Federation
,
Mikhail M. Krayushkin
a
N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, 47 Leninsky prosp., 119991 Moscow, Russian Federation
› Author Affiliations This work was supported by Russian Science Foundation (RSF Grant 14-50-00126).
Abstract
A new chemoselective method for the synthesis of 2-aryl-1,3-oxazoles by deoxygenation of the corresponding N -oxides has been developed. As the deoxygenation reagent, a previously unknown complex of collidine with phosphorus trichloride in a 2:1 ratio has been used. The developed method enabled the preparation of a wide range of 2-aryl-1,3-oxazoles comprising various functional groups in good yields. The advantage of this reagent is its tolerance to nitro, methyl, hydroxyl, formyl, and acetyl groups, and double bonds. Due to chemoselectivity and availability of reagents, the method may be used for deoxygenation of N -oxides of other heterocyclic compounds (thiazole, pyridine, quinoline, etc.).
Key words
deoxygenation -
N -oxides -
azoles -
phosphorus trichloride -
collidine -
chemoselective -
oxazoles
Supporting Information
Supporting information for this article is available online at https://doi.org/10.1055/s-0037-1610278.
Supporting Information
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