Stereoselective Synthesis of endo-7-Halo-3-Oxo-2-Azabicyclo[4.1.0]Heptanes by Reductive Hydrodehalogenation of gem-Dihalocyclopropanes

Author(s): Jomy K. Joseph, Sweety Singhal, Suman L. Jain, Bir Sain

Journal Name: Current Organic Chemistry

Volume 15 , Issue 8 , 2011

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The reduction of 7-gem-dihalo-3-oxo-2-azabicyclo[4.1.0]heptanes with metallic zinc yielded stereoselective synthesis of novel heterocyclic endo-7-halo-3-oxo-2-azabicyclo[4.1.0]heptanes in good to high yields without any evidence for the formation of corresponding exo-isomers. The prepared heterocyclic compounds were characterized by various techniques and their stereochemistry was established on the basis of the values of the coupling constants for H-1, H-5, H-6 and H-7 by recording homonuclear spin-spin decoupled 1H NMR spectra. The developed protocol has many advantages such as simple reaction conditions, lower cost, high yields, and selective synthesis of novel heterocyclic cyclopropyl compounds present in a large number of biologically active natural products and pharmaceuticals compounds.

Keywords: Cyclopropane derivatives, Heterocyclic compound, Monohydrodehalogenation, Reduction, Stereoselective synthesis, bio-medicinal chemistry, monohalocarbene, P-heterocycles, triethyl phosphate, Pharmaceutical, Cinnamaldehyde, Characterization Data, hydroxide, chromatrography, Stereochemistry

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Article Details

Year: 2011
Page: [1230 - 1235]
Pages: 6
DOI: 10.2174/138527211795203059
Price: $58

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