Cascade intramolecular rearrangement/cycloaddition of nitrocyclopropane carboxylates with alkynes/alkenes: access to uncommon bi(hetero)cyclic systems

文献情報

出版日 2021-01-21

DOI 10.1039/D0QO01535K

インパクトファクター 5.281

著者

Rohit Kumar Varshnaya, Priyanka Singh, Navpreet Kaur, Prabal Banerjee

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要旨

A straightforward approach for the one-pot synthesis of aziridinoisoxazoles via cascade intramolecular rearrangement of nitrocyclopropane carboxylates to cyclic nitronates followed by a thermal cycloaddition reaction with substituted phenylacetylenes has been demonstrated. All of the synthesized aziridinoisoxazoles were mostly obtained as single diastereomers, indicating a highly diastereoselective nature of the protocol. Additionally, nitrocyclopropane carboxylates were also made to react with ethyl acrylate to synthesize isoxazolo[2,3-b]isoxazole derivatives in a cascade one-pot fashion. The reactivity of nitrocyclopropane carboxylates with acetylenes and acrylates showed the synthetic divergence of the protocol towards the efficient synthesis of a less explored class of nitrogen heterocycles.

掲載誌

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

Cascade intramolecular rearrangement/cycloaddition of nitrocyclopropane carboxylates with alkynes/alkenes: access to uncommon bi(hetero)cyclic systems

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