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Synthesis 2019; 51(02): 414-420
DOI: 10.1055/s-0037-1610278
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© 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 AffiliationsThis work was supported by Russian Science Foundation (RSF Grant 14-50-00126).
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Publication History

Received: 16 July 2018

Accepted after revision: 23 August 2018

Publication Date:
21 September 2018 (online)

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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.
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