ChemInform Abstract: The Stereoselective Synthesis of Tetrahydrothiopyrano[2,3-b]indole Skeletons via Tandem Reaction of Indoline-2-thiones to Baylis-Hillman Adduct Acetates

Autor:	Behzad Koushki Foroushani, Maryam Sobhani, Firouz Matloubi Moghaddam, Nazila masoud, Mohammad Reza Khodabakhshi, Ng Seik Weng
Rok vydání:	2013
Předmět:	Indole test chemistry.chemical_compound chemistry Cascade reaction Yield (chemistry) Indoline Organic chemistry Stereoselectivity General Medicine Acetonitrile Adduct Catalysis
Zdroj:	ChemInform. 45
ISSN:	0931-7597
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_________::a506e586d136a08077dbb33df0afca71 https://doi.org/10.1002/chin.201402145 Zobrazit plný text záznamu Plný text