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Competitive ways for three-component cyclization of polyfluoroalkyl-3-oxo esters, methyl ketones and amino alcohols

Authors
  • Saloutin, Victor I.1
  • Goryaeva, Marina V.1
  • Kushch, Svetlana O.1
  • Khudina, Olga G.1
  • Ezhikova, Marina A.1
  • Kodess, Mikhail I.1
  • Slepukhin, Pavel A.1
  • Burgart, Yanina V.1
  • 1 Postovsky Institute of Organic Synthesis, Ural Branch, Russian Academy of Sciences, Russian Federation , (Russia)
Type
Published Article
Journal
Pure and Applied Chemistry
Publisher
Walter de Gruyter GmbH
Publication Date
Jul 11, 2020
Volume
92
Issue
8
Pages
1265–1275
Identifiers
DOI: 10.1515/pac-2019-1216
Source
De Gruyter
Keywords
License
Yellow

Abstract

The competitive routes were found for three-component cyclization of polyfluoroalkyl-3-oxo esters, methyl ketones with 3-amino alcohols. It was shown that the reactions with 3-aminopropanol in 1,4-dioxane predominantly lead to hexahydropyrido[2,1-b][1,3]oxazin-6-ones, and in ethanol to 3-hydroxypropylaminocyclohexenones. In contrast, cyclizations with 2-aminoethanol and its analogues, regardless of the reaction conditions, yield hexahydrooxazolo[3,2-a]pyridin-5-ones as the main products. The trans- and cis-diastereomeric structure of heterocycles was established using X-ray and 1H, 19F, 13C NMR spectroscopy, 2D 1H-13C HSQC and HMBC experiments. The mechanism is proposed for competitive transformations of polyfluoroalkyl-3-oxo esters, methyl ketones with 3-amino alcohols.

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