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

Moghaddam, F. M ; Sharif University of Technology | 2013

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  1. Type of Document: Article
  2. DOI: 10.1016/j.tet.2013.07.043
  3. Publisher: 2013
  4. Abstract:
  5. 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%)
  6. Keywords:
  7. Baylis-Hilman adduct acetates ; Indole ; Indoline-2-thione ; Tandem reaction ; Acetic acid derivative ; Indole derivative ; Baylis Hillman reaction ; Catalyst ; Chemical structure ; Priority journal ; Stereochemistry ; Synthesis
  8. Source: Tetrahedron ; Volume 69, Issue 38 , September , 2013 , Pages 8169-8173 ; 00404020 (ISSN)
  9. URL: http://www.sciencedirect.com/science/article/pii/S0040402013011368