229496-83-7Relevant articles and documents
Flow Technology for Telescoped Generation, Lithiation and Electrophilic (C3) Functionalization of Highly Strained 1-Azabicyclo[1.1.0]butanes
Musci, Pantaleo,von Keutz, Timo,Belaj, Ferdinand,Degennaro, Leonardo,Cantillo, David,Kappe, C. Oliver,Luisi, Renzo
supporting information, p. 6395 - 6399 (2021/02/26)
Strained compounds are privileged moieties in modern synthesis. In this context, 1-azabicyclo[1.1.0]butanes are appealing structural motifs that can be employed as click reagents or precursors to azetidines. We herein report the first telescoped continuous flow protocol for the generation, lithiation, and electrophilic trapping of 1-azabicyclo[1.1.0]butanes. The flow method allows for exquisite control of the reaction parameters, and the process operates at higher temperatures and safer conditions with respect to batch mode. The efficiency of this intramolecular cyclization/C3-lithiation/electrophilic quenching flow sequence is documented with more than 20 examples.
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).