title: Gold-catalyzed oxime-oxime rearrangement.
abstract: The gold-catalyzed reaction of pyrrole and indole oximes having a propargyl group attached to the nitrogen atom was studied. The selective 6-endo-dig mode of cyclization was observed for the terminal alkynes giving rise to the formation of pyrazine N-oxides in the presence of a gold catalyst. However, the reaction with substituted alkyne transferred the oxime functionality intramolecularly from one carbon atom to another via the 7-endo-dig cyclization process. This transformation is unprecedented in the literature and is named an oxime-oxime rearrangement.
authors.affiliation: †Department of Chemistry, Middle East Technical University, 06800 Ankara, Turkey.
authors.forename: Sinem
authors.initials: S
authors.lastname: Guven
authors.affiliation: †Department of Chemistry, Middle East Technical University, 06800 Ankara, Turkey.
authors.forename: Merve Sinem
authors.initials: MS
authors.lastname: Ozer
authors.affiliation: †Department of Chemistry, Middle East Technical University, 06800 Ankara, Turkey.|‡Department of Chemistry, Giresun University, 28200 Giresun, Turkey.
authors.forename: Serdal
authors.initials: S
authors.lastname: Kaya
authors.affiliation: †Department of Chemistry, Middle East Technical University, 06800 Ankara, Turkey.|§Faculty of Pharmacy, Yüzüncü Yil University, 65100 Van, Turkey.
authors.forename: Nurettin
authors.initials: N
authors.lastname: Menges
authors.affiliation: †Department of Chemistry, Middle East Technical University, 06800 Ankara, Turkey.
authors.forename: Metin
authors.initials: M
authors.lastname: Balci
mesh_terms: D002384:Catalysis; D006046:Gold / Q000737:chemistry*; D007211:Indoles / Q000737:chemistry; D015394:Molecular Structure; D010091:Oximes / Q000138:chemical synthesis* / Q000737:chemistry; D011758:Pyrroles / Q000737:chemistry
chemical_list: D007211:Indoles; D010091:Oximes; D011758:Pyrroles; D006046:Gold