A facile scheme for phthalimide ⇆ phthalimidine conversion

Frederick A. Luzzio*, De Anna Piatt Zacherl, William D. Figg

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

36 Scopus citations


Desulfurization of phenylthiolactams using an ultrasound-promoted Raney nickel protocol yields the corresponding N-substituted phthalimidines. Benzylic oxidation of the N-substituted phthalimidines by treatment with 2,2'-bipyridinium chlorochromate/m-chloroperbenzoic acid (BPCC/MCPBA) affords the original phthalimides. The reduction-desulfurization is applied to the preparation of a deoxythalidomide derivative which is a TNF-α inhibitor.

Original languageEnglish
Pages (from-to)2087-2090
Number of pages4
JournalTetrahedron Letters
Issue number11
StatePublished - 12 Mar 1999
Externally publishedYes


  • Oxidation
  • Protecting groups
  • Reduction
  • Sonochemistry


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