Synthesis of 3-alkylidene-isoindolinones via sulphide contraction

Xiaoxiang Zhu, Nigel H. Greig, Qian sheng Yu, Tada Utsuki, Harold W. Holloway, Debomoy K. Lahiri, Arnold Brossi

Research output: Contribution to journalArticle

5 Scopus citations


Isoindolinones are essential moieties in numerous natural products, chemical research tools and therapeutics. Syntheses of such isoindoline containing agents may occur through precursors, particularly via 3-alkylidene-isoindolinones. An alternate approach be can achieved via sulphide contraction, described herein. As an example, phthalimide was thionated with Lawesson's reagent to give monothiophthalimide (4), which on stirring with α-bromoketones in the presence of base led to the Eschenmoser coupling reaction. In this manner, compounds (5, 6a and 6b) were formed by alkylation of monothiophthalimide with various α-bromoketones, followed by elimination of sulfur. For the compounds (6a and 6b), (Z)-3-alkylidene-isoindolinones were generated as a single product and no (E)-isomer was separated from the reaction mixture.

Original languageEnglish (US)
Pages (from-to)93-99
Number of pages7
StatePublished - Dec 31 2004

ASJC Scopus subject areas

  • Analytical Chemistry
  • Pharmacology
  • Organic Chemistry

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