Affiliation:
1. Postovsky Institute of Organic Synthesis, Ural Branch, Russian Academy of Sciences , Ekaterinburg , Russian Federation
Abstract
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.
Funder
Russian Foundation for Basic Research
Subject
General Chemical Engineering,General Chemistry
Reference69 articles.
1. J. Zhu, H. Bienayme (Ed.), Multicomponent Reactions, Wiley-VCH Weinheim, Germany (2005).
2. A. Domling. Chem. Rev.106, 17 (2006).
3. B. Ganem. Acc. Chem. Res.42, 463 (2009).
4. A. Domling, W. Wang, K. Wang. Chem. Rev.112, 3083 (2012).
5. J. Liu, J. Li, L. Zhang, L. Song, M. Zhang, W. Cao, S. Zhu, H. Deng, M. Shao. Tetrahedron Lett.53, 2469 (2012).
Cited by
10 articles.
订阅此论文施引文献
订阅此论文施引文献，注册后可以免费订阅5篇论文的施引文献，订阅后可以查看论文全部施引文献