☆ 4.5 Article

Electrophile-Mediated Reactions of Functionalized Propargylic Substrates

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY (2015)

期刊

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY

卷 2015, 期 32, 页码 7091-7113

出版社

WILEY-V C H VERLAG GMBH

DOI: 10.1002/ejoc.201501063

关键词

Alkynes; Electrophilic addition; Cyclization; Nitrogen heterocycles; Sulfur heterocycles; Regioselectivity

类别

Chemistry, Organic

资金

Research Council of Lithuania [MIP-15016]

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Protocol

Reagent

摘要

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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