Synthesis of 3-alkylidene-isoindolinones via sulphide contraction

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

Research output: Contribution to journalArticle

5 Citations (Scopus)

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.

Original languageEnglish
Pages (from-to)93-99
Number of pages7
JournalHeterocycles
Volume64
DOIs
StatePublished - Dec 31 2004

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2,4-bis(4-methoxyphenyl)-1,3,2,4-dithiadiphosphetane-2,4-disulfide
Therapeutic Human Experimentation
Alkylation
Sulfides
Biological Products
Sulfur
Isomers
phthalimide

ASJC Scopus subject areas

  • Organic Chemistry

Cite this

Zhu, X., Greig, N. H., Yu, Q. S., Utsuki, T., Holloway, H. W., Lahiri, D., & 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

Synthesis of 3-alkylidene-isoindolinones via sulphide contraction. / Zhu, Xiaoxiang; Greig, Nigel H.; Yu, Qian sheng; Utsuki, Tada; Holloway, Harold W.; Lahiri, Debomoy; Brossi, Arnold.

In: Heterocycles, Vol. 64, 31.12.2004, p. 93-99.

Research output: Contribution to journalArticle

Zhu, X, Greig, NH, Yu, QS, Utsuki, T, Holloway, HW, Lahiri, D & Brossi, A 2004, 'Synthesis of 3-alkylidene-isoindolinones via sulphide contraction', Heterocycles, vol. 64, pp. 93-99. https://doi.org/10.3987/COM-04-S(P)2
Zhu, Xiaoxiang ; Greig, Nigel H. ; Yu, Qian sheng ; Utsuki, Tada ; Holloway, Harold W. ; Lahiri, Debomoy ; Brossi, Arnold. / Synthesis of 3-alkylidene-isoindolinones via sulphide contraction. In: Heterocycles. 2004 ; Vol. 64. pp. 93-99.
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