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Paper | Special issue | Vol 64, No. 1, 2004, pp.93-99
Published online, 16th November, 2004
DOI: 10.3987/COM-04-S(P)2
Synthesis of 3-Alkylidene-isoindolinones via Sulphide Contraction

Xiaoxiang Zhu, Nigel H. Greig,* Qian-sheng Yu, Tada Utsuki, Harold W. Hollowya, Debomoy K. Lahiri, and Arnold Brossi

*Drug Design & Development, National Institute on Aging Intramural Program, National Institutes of Health, 5600 Nathan Shock Dr., Baltimore, MD 21224-6825, U.S.A.

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.