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 new quinolone antibiotics utilizing azetidine derivatives obtained from 1-azabicyclo[1.1.0]butane
Ikee, Yoshifumi,Hashimoto, Kana,Kamino, Mai,Nakashima, Masaaki,Hayashi, Kazuhiko,Sano, Shigeki,Shiro, Motoo,Nagao, Yoshimitsu
, p. 346 - 356 (2008/12/22)
A series of 3-sulfenylazetidine derivatives 5a-f were synthesized via the ring-opening reactions of 1-azabicyclo[ 1.1.0]butane (ABB, 3) with thiols 4a-f in 50-92% yields. Treatment of ABB (3) with aromatic amines 9a-e and dibenzylamine (9f) in the presence of Mg(ClO4)2 afforded the corresponding 3-aminoazetidine derivatives 10a-f in 24-65% yields. N-Benzyl-3-bromoazetidine (13), which was obtained by the reaction of ABB (3) with benzyl bromide, gave 3-aliphatic amino-substituted azetidine derivatives 15a, b. Novel fluoroquinolones 7a-f, 11a-f, 16a, b and 25a-c were obtained by the introduction of these azetidine derivatives into the C7 position of a quinolone nucleus 6 and N1-heterocyclic quinolones 21a-c in 21-83% yields. Some of them exhibited a greater antibacterial activity against methicillin-resistant Staphylococcus aureus (MRSA) in comparison with that of clinically used fluoroquinolone, levofloxacin (LVFX).
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).
Novel efficient synthesis of 1-azabicyclo[1.1.0]butane and its application to the synthesis of 1-(1,3-thiazolin-2-yl)azetidine-3-thiol useful for the pendant moiety of an oral 1β-methyicarbapenem antibiotic L- 084
Hayashi, Kazuhiko,Sato, Chisato,Hiki, Shinsuke,Kumagai, Toshio,Tamai, Satoshi,Abe, Takao,Nagao, Yoshimitsu
, p. 3761 - 3764 (2007/10/03)
1-Azabicyclo[1.1.0]butane 2 was successfully synthesized by treatment of 2,3dibromopropylamine hydrobromide 4 with organolithium compounds and was readily converted to 1-(1,3-thiazolin-2-yl)azetidine-3-thiol hydrochloride 1 and versatile azetidine derivatives 9 and 10.
