title: PIFA-BF3·OEt2mediated intramolecular regioselective domino cyclization of ynamides: A novel method for the synthesis of tetrahydroisoquinoline-oxazol-2(3H)-ones.
abstract: The transition metal-free intramolecular regioselective domino cyclization of N-Boc protected ynamides has been developed to provide the corresponding tetrahydroisoquinoline-oxazo-2(3H)-ones in moderate to good yields.
authors.affiliation: Laboratory of Medicinal Chemistry, Chulabhorn Research Institute, 54 Kamphaeng Phet 6 Road, Laksi, Bangkok 10210, Thailand. Electronic address: winai@cri.or.th.
authors.forename: Winai
authors.initials: W
authors.lastname: Ieawsuwan
authors.affiliation: Laboratory of Medicinal Chemistry, Chulabhorn Research Institute, 54 Kamphaeng Phet 6 Road, Laksi, Bangkok 10210, Thailand; Chemical Biology Program, Chulabhorn Graduate Institute, 54 Kamphaeng Phet 6 Road, Laksi, Bangkok 10210, Thailand; Center of Excellence on Environmental Health and Toxicology (EHT), Ministry of Education, 54 Kamphaeng Phet 6 Road, Laksi, Bangkok 10210, Thailand.
authors.forename: Somsak
authors.initials: S
authors.lastname: Ruchirawat
mesh_terms: D000085:Acetates / Q000737:chemistry*; D000480:Alkynes / Q000737:chemistry*; D000577:Amides / Q000737:chemistry*; D001880:Boranes / Q000737:chemistry; D003500:Cyclization; D004986:Ether / Q000737:chemistry; D007462:Iodobenzenes / Q000737:chemistry*; D007546:Isoquinolines / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D010080:Oxazoles / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism
chemical_list: D000085:Acetates; D000480:Alkynes; D000577:Amides; D001880:Boranes; D007462:Iodobenzenes; D007546:Isoquinolines; D010080:Oxazoles; D004986:Ether; C407568:(bis(trifluoroacetoxy)iodo)benzene; C021274:boron trifluoride
keywords: Domino cyclization; Hypervalent iodine; Oxazol-2(3H)-one; Tetrahydroisoquinoline; Ynamide