The stereoselective synthesis of tetrahydrothiopyrano[2,3-b]indole skeletons via tandem reaction of indoline-2-thiones to Baylis-Hillman adduct acetates

Firouz Matloubi Moghaddam*, Behzad Koushki Foroushani, Maryam Sobhani, Nazila Masoud, Mohammad Reza Khodabakhshi, Ng Seik Weng

*Corresponding author for this work

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8 Citations (Scopus)

Abstract

Indoline-2-thiones (5) were applied as 1,3-dinucleophiles in a tandem reaction with Baylis-Hillman adduct acetates (4) to give novel tetrahydrothiopyrano[2,3-b]indole skeletons (6). The effect of different solvents, bases, and catalysts on the yields and stereochemical outcome was studied in detail. The results indicated that acetonitrile as solvent and K 2CO3 as base, under reflux conditions, were the optimum conditions. Products 6a-6l were obtained in high diastereoselectivity and yield (up to 94%).

Original languageEnglish
Pages (from-to)8169-8173
JournalTetrahedron
Volume69
Issue number38
DOIs
Publication statusPublished - 23 Sep 2013
Externally publishedYes

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Keywords

  • Baylis-Hilman adduct acetates
  • Indole
  • Indoline-2-thione
  • Tandem reaction

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