Journal
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
Volume 2015, Issue 32, Pages 7091-7113Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/ejoc.201501063
Keywords
Alkynes; Electrophilic addition; Cyclization; Nitrogen heterocycles; Sulfur heterocycles; Regioselectivity
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Funding
- Research Council of Lithuania [MIP-15016]
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Metal-free halogen, chalcogen, or oxocarbenium ion mediated yne-carbonyl or yne-thioxo transformations of a range of N- and O-propargylic compounds have been studied. This investigation has led to the development of a mild, economic, and effective method for the synthesis of functionalized 4H-1,3-oxazines, 4H-1,3-thiazines, 4,5-dihydrothiazoles, and alpha-substituted enones. The structure of the propargylic substrate and the nature of electrophile influence both the outcome and regioselectivity of processes.
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