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

Abstract

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.

ASJC Scopus subject areas

  • Analytical Chemistry
  • Pharmacology
  • Organic Chemistry

Cite this

Zhu, X., Greig, N. H., Yu, Q. S., Utsuki, T., Holloway, H. W., Lahiri, D. K., & Brossi, A. (2004). Synthesis of 3-alkylidene-isoindolinones via sulphide contraction. Heterocycles, 64, 93-99. https://doi.org/10.3987/COM-04-S(P)2