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Paper | Special issue | Vol 56, No. 1-2, 2002, pp.433-442
Published online, 1st January, 1970
DOI: 10.3987/COM-01-S(K)65
Synthesis of Azetidine Derivatives Using 1-Azabicyclo[1.1.0]butane

Kazuhiko Hayashi, Shinsuke Hiki, Toshio Kumagai, and Yoshimitsu Nagao*

*Faculty of Pharmaceutical Sciences, University of Tokushima, Sho-machi, Tokushima 770-8505, Japan


A THF solution of 1-azabicyclo[1.1.0]butane (2), obtained from 2,3-dibromopropylamine hydrobromide (1), was treated with HCl-EtOH, 48% HBr, ClCO2Et, Ts2O, HCO2H - 2.7N HCl-MeOH, or Ac2O - 3N HCl to give the corresponding 3-monosubstituted and 1,3-disubstituted azetidine derivatives (3-7). Similar treatment of 2 with AcSH afforded 1-acetyl-3-acetylthioazetidine (8), which was converted to 1-(1,3-thiazolidin-2-yl)azetidine-3-thiol hydrochloride (10). The compound (2) and various bromides were heated to furnish 3-bromoazetidine derivatives (12b,c,e,f) and/or N,N-disubstituted 2,3-dibromopropylamines (13a,c-f). The reaction of 2 with benzoyl peroxide or N-bromosuccinimide gave each corresponding 1,3-disubustituted azetidine derivative (14 or 15).