25755-89-9Relevant academic research and scientific papers
Iron dichloride induced isomerization or reductive cleavage of isoxazoles: A facile synthesis of 2-carboxy-azirines
Auricchio, Sergio,Bini, Antonella,Pastormerlo, Eros,Truscello, Ada M.
, p. 10911 - 10920 (1997)
5-Alkoxy-isoxazoles and N,N-disubstituted-5-isoxazolamines were found to isomerize to azirine derivatives by the use of iron dichloride as catalyst. On the contrary 5-alkyl- and 5-aryl-isoxazoles in the presence of the same salt, undergo reductive cleavage to enaminoketones. A common reaction intermediate is proposed.
An Azirine Strategy for the Synthesis of Alkyl 4-Amino-5-(trifluoromethyl)-1 H -pyrrole-2-carboxylates
Funt, Liya D.,Tomashenko, Olesya A.,Novikov, Mikhail S.,Khlebnikov, Alexander F.
, p. 4809 - 4822 (2018/12/13)
1-(3,3,3-Trifluoro-2,2-dihydroxypropyl)pyridin-1-ium bromide serves as a trifluoromethyl-containing building block for the preparation of trifluoromethyl-substituted aminopyrroles based on the 2 H -azirine ring expansion strategy. The primary products, 3-
A novel approach to 5: H -pyrazino[2,3- b] indoles via annulation of 3-diazoindolin-2-imines with 2 H -azirines or 5-alkoxyisoxazoles under Rh(II) catalysis
Ruvinskaya, Julia O.,Rostovskii, Nikolai V.,Filippov, Ilya P.,Khlebnikov, Alexander F.,Novikov, Mikhail S.
supporting information, p. 38 - 42 (2017/12/27)
A novel one-step method for the preparation of 5H-pyrazino[2,3-b]indoles with different substitution patterns in all rings of the tricyclic system via the Rh2(OAc)4-catalyzed reaction of 2H-azirines with 3-diazoindolin-2-imines is reported. Alkyl 5H-pyrazino[2,3-b]indole-3-carboxylates were also prepared by a one-pot procedure from synthetic equivalents of alkyl 2H-azirine-2-carboxylates, 5-alkoxyisoxazoles. The reactions provide the first examples of the use of Rh(ii) catalysis for intermolecular annulations with 2H-azirines and isoxazoles.
