Reactivity of epoxy-ynamides with metal halides: nucleophile (Br/Cl/OH)-assisted tandem intramolecular 5-exo-dig or 6-endo-dig cyclisation and AgF2-promoted oxidation

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出版日 2019-02-21

DOI 10.1039/C9QO00027E

インパクトファクター 5.281

著者

Mandala Anitha, Mallepalli Shankar, K. C. Kumara Swamy

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要旨

Several metal halides react with epoxy-ynamides. Thus, CuBr-mediated concomitant bromination/5-exo-dig cyclisation of epoxy-ynamides affords functionalised 1,3-oxazolidines. In contrast, functionalised 1,4-oxazines are obtained via 6-endo-dig cyclisation of epoxy-ynamides using LiCl or CuF2/H2O. In addition, CuBr is effective for dibromination of functionalised ynamides leading to α,β-dibromo-enamides, with the (E) isomer predominating. Formation of epoxy-1,2-dioxo-amides by oxidation of epoxy-ynamides using AgF2 as the oxidising agent is also highlighted.

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Organic Chemistry Frontiers

CiteScore: 7.8

自己引用率: 8.7%

年間論文数: 724

Organic Chemistry Frontiers publishes high-quality research from across organic chemistry. Emphases are placed on studies that make significant contributions to the field of organic chemistry by reporting either new or significantly improved protocols or methodologies. Topics include, but are not limited to the following: Organic synthesis Development of synthetic methodologies Catalysis Natural products Functional organic materials Supramolecular and macromolecular chemistry Physical and computational organic chemistry

Reactivity of epoxy-ynamides with metal halides: nucleophile (Br/Cl/OH)-assisted tandem intramolecular 5-exo-dig or 6-endo-dig cyclisation and AgF2-promoted oxidation

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