title: Facile synthesis of azaspirocycles via iron trichloride-promoted cyclization/chlorination of cyclic 8-aryl-5-aza-5-tosyl-2-en-7-yn-1-ols.
abstract: A simple and efficient FeCl(3)-promoted cyclization/chlorination of cyclic tosylamine-tethered 8-aryl-2-en-7-yn-1-ols was observed. The reaction proceeded instantaneously at 23 °C in air to afford (Z)-4-(arylchloromethylene)-substituted azaspirocycles in good to excellent yields. This transformation can also be applied to the synthesis of spirocarbocyclic analogues from cyclic 8-aryl-2-en-7-yn-1-ols and FeCl(3).
authors.affiliation: Department of Chemistry, National Taiwan Normal University, 88 Ding-Jou Road, Section 4, Taipei 11677, Taiwan, Republic of China. cheyeh@ntnu.edu.tw
authors.forename: Ming-Chang P
authors.initials: MC
authors.lastname: Yeh
authors.forename: Cheng-Wei
authors.initials: CW
authors.lastname: Fang
authors.forename: Hsin-Hui
authors.initials: HH
authors.lastname: Lin
mesh_terms: D000480:Alkynes / Q000737:chemistry*; D002384:Catalysis; D002712:Chlorides / Q000737:chemistry*; D003500:Cyclization; D005290:Ferric Compounds / Q000737:chemistry*; D054879:Halogenation; D015394:Molecular Structure; D011759:Pyrrolidines / Q000138:chemical synthesis* / Q000737:chemistry; D013141:Spiro Compounds / Q000138:chemical synthesis* / Q000737:chemistry
chemical_list: D000480:Alkynes; D002712:Chlorides; D005290:Ferric Compounds; D011759:Pyrrolidines; D013141:Spiro Compounds; C024555:ferric chloride