245-47-6Relevant academic research and scientific papers
One-Pot Protocol to Synthesize 2-Aminophenols from Anilines via Palladium-Catalyzed C-H Acetoxylation
Zhao, Junhao,Huang, Yifeng,Ma, Guojian,Lin, Ling,Feng, Pengju
, p. 2084 - 2091 (2019/05/21)
This paper describes a facile one-pot protocol to synthesize 2-aminophenol derivatives via a palladium-catalyzed C-H acetoxylation strategy with 5-nitropyrimidine as a directing group (DG), which can be easily preinstalled and readily removed under mild condition after the coupling. In addition, the transformation is operationally simple, has high functional group tolerance, and is amenable to gram-scale. Moreover, several examples were shown that introduction/removal of 5-nitropyrimidine and the C-H oxylation sequence could be integrated in one pot.
A metal-free tandem demethylenation/C(sp2)-H cycloamination process of N -Benzyl-2-aminopyridines via C-C and C-N bond cleavage
Liang, Dongdong,He, Yimiao,Liu, Lanying,Zhu, Qiang
supporting information, p. 3476 - 3479 (2013/07/26)
A mild, metal-free synthesis of pyrido[1,2-a]benzimidazoles starting with N-benzyl-2-aminopyridines, which employs PhI(OPiv)2 as a stoichiometric oxidant, has been developed. The process is initiated by an unusual PhI(OPiv)2-mediated ipso SEAr reaction, followed by solvent-assisted C-C and C-N bond cleavage.
Effect of methanesulfonyl group on the regioselectivity of photocyclization of arylheterylamine derivatives
Frolov
, p. 1254 - 1261 (2007/10/03)
Irradiation of arylheterylamines with a methanesulfonyl leaving group ortho to the amino group produces nonselective cyclization to form either a C-C (arylpyridylamines) or a C-N (arylpyrimidylamines) bond. When the methanesulfonyl group is a substituent and chlorine is a leaving group, regioselective photocyclization is observed with C-N bond formation. New pyrido- and pyrimido[1,2-a]benzimidazole derivatives with a methanesulfonyl group in the benzene ring, as well as pyrimido[1,2-a]perimidine derivatives are described. The different regioselectivity of photocyclization of these classess of compounds is explained in terms of radical-cation and electrocyclic reaction mechanisms.
