|Title||The stereoselective synthesis of tetrahydrothiopyrano[2,3-b]indole skeletons via tandem reaction of indoline-2-thiones to Baylis-Hillman adduct acetates|
|Author(s)||Moghaddam, Firouz Matloubi; Foroushani, Behzad Koushki; Sobhani, Maryam; Masoud, Nazila; Khodabakhshi, Mohammad Reza; Weng, Ng Seik|
|Source||Tetrahedron 69 (2013)38. - ISSN 0040-4020 - p. 8169 - 8173.|
|Publication type||Refereed Article in a scientific journal|
|Keyword(s)||Baylis-Hilman adduct acetates - Indole - Indoline-2-thione - Tandem reaction|
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%).