One-Pot Metal-Free Synthesis of 3-CF3-1,3-Oxazinopyridines by Reaction of Pyridines with CF3CO-Acetylenes

Vasiliy  M. Muzalevskiy; Zoia  A. Sizova; Kseniya  V. Belyaeva; Boris  A. Trofimov; Valentine  G. Nenajdenko

doi:10.3390/molecules24193594

Molecules (Oct 2019)

One-Pot Metal-Free Synthesis of 3-CF3-1,3-Oxazinopyridines by Reaction of Pyridines with CF3CO-Acetylenes

Vasiliy M. Muzalevskiy,
Zoia A. Sizova,
Kseniya V. Belyaeva,
Boris A. Trofimov,
Valentine G. Nenajdenko

Affiliations

Vasiliy M. Muzalevskiy: M. V. Lomonosov Moscow State University, Department of Chemistry, Leninskie Gory 1, 119991 Moscow, Russia
Zoia A. Sizova: M. V. Lomonosov Moscow State University, Department of Chemistry, Leninskie Gory 1, 119991 Moscow, Russia
Kseniya V. Belyaeva: A. E. Favorsky Irkutsk Institute of Chemistry, Siberian Branch, Russian Academy of Sciences, 1 Favorsky Str., 664033 Irkutsk, Russia
Boris A. Trofimov: A. E. Favorsky Irkutsk Institute of Chemistry, Siberian Branch, Russian Academy of Sciences, 1 Favorsky Str., 664033 Irkutsk, Russia
Valentine G. Nenajdenko: M. V. Lomonosov Moscow State University, Department of Chemistry, Leninskie Gory 1, 119991 Moscow, Russia

DOI: https://doi.org/10.3390/molecules24193594
Journal volume & issue: Vol. 24, no. 19
p. 3594

Abstract

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The reaction of pyridines with trifluoroacetylated acetylenes was investigated. It was found that the reaction of various pyridines with two molecules of CF3CO-acetylenes proceeds under mild metal-free conditions. As a result, efficient stereoselective synthesis of 3-arylethynyl-3-trifluoromethyl-1,3-oxazinopyridines was elaborated. Target heterocycles can be prepared in up to quantitative yields.

Published in Molecules

ISSN: 1420-3049 (Online)
Publisher: MDPI AG
Country of publisher: Switzerland
LCC subjects: Science: Chemistry: Organic chemistry
Website: http://www.mdpi.com/journal/molecules

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