Jump to main content
Jump to site search


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

Author affiliations

Abstract

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.

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

Back to tab navigation

Supplementary files

Article information


Submitted
07 Dec 2020
Accepted
21 Jan 2021
First published
21 Jan 2021

Org. Chem. Front., 2021, Advance Article
Article type
Research Article

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

R. K. Varshnaya, P. Singh, N. Kaur and P. Banerjee, Org. Chem. Front., 2021, Advance Article , DOI: 10.1039/D0QO01535K

Social activity

Search articles by author

Spotlight

Advertisements