Base-promoted highly efficient synthesis of nitrile-substituted cyclopropanes via Michael-initiated ring closure† † Electronic supplementary information (ESI) available: Experimental section, characterization of all compounds, copies of 1H and 13C NMR spectra for selected compounds. CCDC 2141258 and 2142244. For ESI and crystallographic data in CIF or other electronic format see DOI: https://doi.org/10.1039/d2ra05393d

ABSTRACT: A convenient and efficient annulation reaction has been developed for the general synthesis of dinitrile-substituted cyclopropanes in moderate to excellent yields. A variety of 2-arylacetonitriles and α-bromoennitriles were compatible under the standard conditions. The reaction was achieved through tandem Michael-type addition followed by intramolecular cyclization. The preliminary application of this method was confirmed by the synthesis of the 2,4-dioxo-3-azabicyclo[3.1.0]hexane scaffold. An efficient base-promoted synthesis of nitrile-substituted cyclopropanes from 2-arylacetonitriles and α-bromoennitriles under mild conditions via Michael-initiated ring closure.

SUBMITTER: Ye M 

PROVIDER: S-EPMC9536251 | biostudies-literature | 2022 Oct

REPOSITORIES: biostudies-literature