420820-69-5Relevant academic research and scientific papers
New Synthesis of Propargylic Amines from 2-(Bromomethyl)aziridines. Intermediacy of 3-Bromoazetidinium Salts
D'Hooghe, Matthias,Van Brabandt, Willem,De Kimpe, Norbert
, p. 2703 - 2710 (2007/10/03)
A new, efficient, and straightforward synthesis provides propargylamines in high overall yields (64-77%) by transformation of 1-(arylmethyl)-2-(bromomethyl)aziridines into N,N-di(arylmethyl)N-(2-propynyl)amines via N-(2,3-dibromopropyl)amines and N-(2-bromo-2-propenyl)amines. The conversion of N-(2,3-dibromopropyl)amines into N-(2-bromo-2-propenyl)amines is based on a novel analogue of the Hofmann elimination. A Yamaguchi-Hirao alkylation, a Sonogashira coupling, or a hydroarylation reaction further functionalized these propargylamines toward potentially interesting compounds for medicinal and agrochemical use.
Synthesis of azetidine derivatives using 1-azabicyclo[1.1.0]butane
Hayashi, Kazuhiko,Hiki, Shinsuke,Kumagai, Toshio,Nagao, Yoshimitsu
, p. 433 - 442 (2007/10/03)
A THF solution of 1-azabicyclo[1.1.0]butane (2), obtained from 2,3-dibromopropylamine hydrobromide (1), was treated with HC1-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).
