1107023-82-4Relevant academic research and scientific papers
Electrochemical synthesis of benzoxazoles from anilides-a new approach to employ amidyl radical intermediates
Gieshoff, Tile,Kehl, Anton,Schollmeyer, Dieter,Moeller, Kevin D.,Waldvogel, Siegfried R.
, p. 2974 - 2977 (2017)
A novel electrochemical method for the synthesis of benzoxazoles from readily available anilides is reported. Various functionalities are tolerated and good yields can be achieved. By employing common electrode materials and a simple constant current protocol, this method is an attractive new alternative to conventional pathways.
Divergent reactivities of o-haloanilides with CuO nanoparticles in water: A green synthesis of benzoxazoles and o-hydroxyanilides
Khatun, Nilufa,Guin, Srimanta,Rout, Saroj Kumar,Patel, Bhisma K.
, p. 10770 - 10778 (2014/03/21)
In the present study, three divergent reaction paths emerged when o-haloanilides were subjected to CuO nanoparticles in water. o-Halo (I, Br) phenylbenzamides in the presence of CuO nanoparticles and Cs2CO 3 in water at 100 °C provided o-hydroxyphenyl benzamides as the major product. However, a complete change in selectivity was observed in the presence of an organic base/ligand (TMEDA), giving 2-arylbenzoxazole as the exclusive product. The above selectivities were not clearly distinct when the corresponding alkylamides were treated either in the presence or absence of the ligand. A number of o-halophenyl alkylamides provided either exclusively o-dehalogenated products or a mixture of o-dehalogenated and o-hydroxylated products, but none gave 2-alkylbenzoxazoles. In addition to the above selectivities, the use of an environmentally friendly solvent (water) and base, and the recyclability of the catalyst make this procedure a benign alternative to the existing methods for the synthesis of these molecules, viz. o-hydroxybenzamides and o-arylbenzoxazoles.
