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

Autor:	Ng Seik Weng, Nazila masoud, Mohammad Reza Khodabakhshi, Behzad Koushki Foroushani, Firouz Matloubi Moghaddam, Maryam Sobhani
Rok vydání:	2013
Předmět:	Indole test Baylis-Hilman adduct acetates Organic Chemistry Indoline-2-thione Biochemistry Medicinal chemistry Adduct Catalysis chemistry.chemical_compound chemistry Cascade reaction Indole Yield (chemistry) Drug Discovery Indoline Tandem reaction Stereoselectivity Acetonitrile
Zdroj:	Tetrahedron 69 (2013) 38 Tetrahedron, 69(38), 8169-8173
ISSN:	0040-4020
Popis:	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 2 CO 3 as base, under reflux conditions, were the optimum conditions. Products 6a – 6l were obtained in high diastereoselectivity and yield (up to 94%).
Databáze:	OpenAIRE
Externí odkaz:	https://explore.openaire.eu/search/publication?articleId=doi_dedup___::7eb7618641af3439767b0c73f5bb1de7 https://doi.org/10.1016/j.tet.2013.07.043 Zobrazit plný text záznamu Full Text from ScienceDirect