16394-40-4Relevant articles and documents
Ruthenium(II)-Catalyzed Regioselective C-8 Hydroxylation of 1,2,3,4-Tetrahydroquinolines
Chen, Changjun,Pan, Yixiao,Zhao, Haoqiang,Xu, Xin,Luo, Zhenli,Cao, Lei,Xi, Siqi,Li, Huanrong,Xu, Lijin
supporting information, p. 6799 - 6803 (2018/11/21)
Ru(II)-catalyzed chelation-assisted highly regioselective C8-hydroxylation of 1,2,3,4-tretrahydroquinolines has been developed. Various 1,2,3,4-tetrahydroquinolines underwent smooth C8-H hydroxylation with cheap and safe K2S2O8 as the oxidant and oxygen source to furnish the corresponding products in good to excellent yields with high tolerance of the functional groups. The choice of a readily installable and removable N-pyrimidyl directing group is the key to catalysis. Mechanistic studies suggest the involvement of a six-membered ruthenacycle intermediate in the catalytic cycle. The method can also be extended to the direct hydroxylation of other (hetero)arene C-H bonds.
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.
Oxidation-reduction reactions of N-sulfonoxyacetanilides: Mechanisms of the halide-induced reduction of models for the carcinogenic metabolites of aromatic amides
Pelecanou,Novak
, p. 4499 - 4503 (2007/10/02)
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