39123-58-5Relevant academic research and scientific papers
Benzo-Fused 1,4-Heterocycles via Dialkyl Carbonate Chemistry
Musolino, Manuele,Aricò, Fabi
, p. 1770 - 1778 (2019/04/05)
A novel halogen-free synthesis of benzo-fused six-membered 1,4-heterocycles through the chemistry of dialkyl carbonates is reported. Commercially available catechol, 2-aminophenol, and 2-aminothiophenol were reacted first with ethylene carbonate in an autoclave to give O -hydroxyethyl, N -hydroxyethyl, and S -hydroxyethyl derivatives respectively, through a B Al 2 mechanism. Then 2-(2-hydroxyethoxy)phenol and 2-(2-hydroxyethylamino)phenol were cyclized in excellent yields by reaction with dimethyl carbonate (DMC) and DABCO as a bicyclic organic base to give the corresponding benzodioxine and benzoxazine derivative, respectively. Moreover, 2-(2-aminophenylthio)ethanol afforded the benzothiazine derivative in good yield by reaction with DMC with an excess of a strong base such as NaH. The investigation on the cyclization reaction has highlighted that several equilibria are involved leading to the formation of carbonate and carbamate intermediates through B Ac 2 mechanisms. Depending on the reaction conditions employed, these intermediates may undergo either kinetic-controlled ring closure by a B Al 2 mechanism or by-product formation.
Facile synthesis of aminoalcohols by ring opening of epoxides under solvent free conditions
Huerta, Gloria,Contreras-Ordonez, Guadalupe,Alvarez-Toledano,Santes, Victor,Gomez, Elizabeth,Toscano, Ruben A.
, p. 2393 - 2406 (2007/10/03)
The convenient cleavage of symmetrical and unsymmetrical epoxides with either aromatic or aliphatic amine under solvent free conditions is reported. The reactions were carried out in a sealed ampoule at 90°C to give regioselectively the corresponding β-amino alcohol in one pot in high yields.
