title: Scandium-catalyzed tandem selective oxirane ring-opening/Friedel-Crafts alkylation: a facile access to [1,4]oxazino[4,3-a]indoles and 3,4-dihydro-1H-pyrrolo[2,1-c][1,4]oxazines.
abstract: A facile technique involving a novel Lewis-acid-catalyzed tandem selective ring-opening of oxirane and Friedel-Crafts alkylation of 1H-indol-1-yl derived oxiranes was developed. The developed protocol affords functionalized [1,4]oxazino[4,3-a]indoles and 3,4-dihydro-1H-pyrrolo[2,1-c][1,4]oxazines in up to 95% yield.
authors: Shanghai Key Laboratory of Green Chemistry and Chemical Processes, Department of Chemistry, East China Normal University, 3663 North Zhongshan Road, Shanghai 200062, China. lliu@chem.ecnu.edu.cn jlzhang@chem.ecnu.edu.cn.
authors: Lai
authors: L
authors: Wei
authors: Lu
authors: L
authors: Liu
authors: Junliang
authors: J
authors: Zhang
mesh_terms: D000478:Alkylation; D000975:Antioxidants / Q000737:chemistry; D002384:Catalysis; D002625:Chemistry, Organic / Q000379:methods*; D002626:Chemistry, Pharmaceutical / Q000379:methods; D003500:Cyclization; D015195:Drug Design; D005027:Ethylene Oxide / Q000737:chemistry; D006801:Humans; D007211:Indoles / Q000737:chemistry*; D008297:Male; D008956:Models, Chemical; D008968:Molecular Conformation; D015394:Molecular Structure; D010078:Oxazines / Q000737:chemistry*; D011472:Prostatitis / Q000188:drug therapy; D012538:Scandium / Q000737:chemistry*; D013237:Stereoisomerism
chemical_list: D000975:Antioxidants; D007211:Indoles; D010078:Oxazines; D005027:Ethylene Oxide; D012538:Scandium