title: Utility of Nitrogen Extrusion of Azido Complexes for the Synthesis of Nitriles, Benzoxazoles, and Benzisoxazoles.
abstract: The utility of the nitrogen extrusion reaction of azido complexes, generated in situ from the corresponding aldehydes or ketones with TMSN3 in the presence of ZrCl4 or TfOH, has been described. These azido complexes could undergo three different pathways, depending on the substrates. First, azido methanolate complexes or imine diazonium ions could lead to benzisoxazole products via an intramolecular nucleophilic substitution. Second, imine diazonium ions could also undergo either the elimination of proton to provide nitrile products in good to excellent yields or an aryl migration, followed by an intramolecular nucleophilic addition, to give benzoxazole products in good yields.
authors.affiliation: Program on Chemical Biology, Center of Excellence on Environmental Health and Toxicology (EHT), Ministry of Education, Chulabhorn Graduate Institute , 54 Kamphaeng Phet 6, Laksi, Bangkok 10210, Thailand.
authors.forename: Phongprapan
authors.initials: P
authors.lastname: Nimnual
authors.affiliation: Program on Chemical Biology, Center of Excellence on Environmental Health and Toxicology (EHT), Ministry of Education, Chulabhorn Graduate Institute , 54 Kamphaeng Phet 6, Laksi, Bangkok 10210, Thailand.|Laboratory of Medicinal Chemistry, Chulabhorn Research Institute , 54 Kamphaeng Phet 6, Laksi, Bangkok 10210, Thailand.
authors.forename: Jumreang
authors.initials: J
authors.lastname: Tummatorn
authors.affiliation: Program on Chemical Biology, Center of Excellence on Environmental Health and Toxicology (EHT), Ministry of Education, Chulabhorn Graduate Institute , 54 Kamphaeng Phet 6, Laksi, Bangkok 10210, Thailand.|Laboratory of Medicinal Chemistry, Chulabhorn Research Institute , 54 Kamphaeng Phet 6, Laksi, Bangkok 10210, Thailand.
authors.forename: Charnsak
authors.initials: C
authors.lastname: Thongsornkleeb
authors.affiliation: Program on Chemical Biology, Center of Excellence on Environmental Health and Toxicology (EHT), Ministry of Education, Chulabhorn Graduate Institute , 54 Kamphaeng Phet 6, Laksi, Bangkok 10210, Thailand.|Laboratory of Medicinal Chemistry, Chulabhorn Research Institute , 54 Kamphaeng Phet 6, Laksi, Bangkok 10210, Thailand.
authors.forename: Somsak
authors.initials: S
authors.lastname: Ruchirawat