99073-85-5Relevant academic research and scientific papers
A novel strategy for the synthesis of thermally stable and apoptosis-inducing 2,3-dihydroazetes
Smetanin, Ilia A.,Novikov, Mikhail S.,Agafonova, Anastasiya V.,RostovskII, Nikolai V.,Khlebnikov, Alexander F.,Kudryavtsev, Igor V.,Terpilowski, Maxim A.,Serebriakova, Maria K.,Trulioff, Andrey S.,Goncharov, Nikolay V.
, p. 4479 - 4487 (2016)
A general and concise approach to thermally and hydrolytically stable alkyl 2,3-dihydroazete-2,3-di-/2,2,3-tricarboxylates from alkyl 2-bromoazirine-2-carboxylates or 4-bromo-5-alkoxyisoxazoles is reported. The synthesis involves the formation of 2-azabut
Easy Access to 2-Fluoro- And 2-Iodo-2 H -azirines via the Halex Reaction
Agafonova, Anastasiya V.,Khlebnikov, Alexander F.,Novikov, Mikhail S.,Rostovskii, Nikolai V.,Smetanin, Ilia A.
, p. 4582 - 4589 (2019/12/11)
A simple gram-scale method for the preparation of esters and dialkylamides of 2-(fluoro/iodo)-2 H -azirine-2-carboxylic acids via the halogen exchange (Halex) reaction of 2-bromo-substituted analogues is reported. The method operates with inexpensive and safe reagents, Bu 4 NF and potassium iodide, providing high product yields. Alternatively, 2-fluoro-2 H -azirine-2-carboxylates can be prepared from 2-iodo- and 2-chloro-analogues. The latter compounds can be obtained in practically quantitative yield by treating the 2-iodo- and 2-bromo-2 H -azirine-2-carboxylic esters with Bu 4 NCl.
Metal-Catalyzed Isomerization of 5-Heteroatom-Substituted Isoxazoles as a New Route to 2-Halo-2 H -azirines
Rostovskii, Nikolai V.,Agafonova, Anastasiya V.,Smetanin, Ilia A.,Novikov, Mikhail S.,Khlebnikov, Alexander F.,Ruvinskaya, Julia O.,Starova, Galina L.
, p. 4478 - 4488 (2017/09/26)
A convenient gram-scale method for the preparation of 2-halo-2 H -azirine-2-carboxylic acid esters, thioesters and amides via metal-catalyzed isomerization of 5-heteroatom-substituted 4-haloisoxazoles is developed. The formation of the esters and amides is efficiently catalyzed by Rh 2 (Piv) 4, while FeCl 2 ·4H 2 O is the catalyst of choice for the synthesis of the thioesters. In addition, rhodium catalysis is successfully applied in the synthesis of azirine-2-carboxylates from non-halogenated 5-alkoxyisoxazoles.
