26332-63-8Relevant academic research and scientific papers
Synthesis of 3,6-Dihydro-2H-[1, 2]-Oxazines from Nitroarenes and Conjugated Dienes, Catalyzed by Palladium/Phenanthroline Complexes and Employing Phenyl Formate as a CO Surrogate
EL-Atawy, Mohamed A.,Formenti, Dario,Ferretti, Francesco,Ragaini, Fabio
, p. 4707 - 4717 (2018/09/25)
Palladium/phenanthroline catalyzed reduction of nitroarenes by in situ-generated carbon monoxide, from the decomposition of phenyl formate, affords the corresponding nitrosoarenes. The latter are trapped by conjugated dienes to give the corresponding 3,6-dihydro-2H-[1, 2]-oxazines (hetero Diels-Alder adducts). Many functional groups are well tolerated. Yields are higher than those obtainable by any previously reported method, including the direct reaction of the diene with the pure nitrosoarene. The reaction can be performed in a single standard glass pressure tube, without the need for autoclaves or high-pressure CO lines.
Iron-catalyzed allylic C-H amination of substituted 1,3-dienes
Murru, Siva,Srivastava, Radhey S.
, p. 2174 - 2181 (2014/04/17)
A catalytic method for the selective allylic C-H amination of dienes and trienes using arylhydroxylamines has been developed. This iron-catalyzed approach involves the in situ generation of activated nitrosoarenes, which in turn react with dienes or trienes to give the corresponding aminomethyl dienes or trienes as the major products, and hetero-Diels-Alder adducts as minor products. The selectivity depends on the structures of both the catalyst and the substrate. We have also studied substituent effects using p-substituted phenylhydroxylamines. Copyright
Synthesis of oxazines and N-arylpyrroles by reaction of unfunctionalized dienes with nitroarenes and carbon monoxide, catalyzed by palladium-phenanthroline complexes
Ragaini, Fabio,Cenini, Sergio,Brignoli, Daniela,Gasperini, Michela,Gallo, Emma
, p. 460 - 466 (2007/10/03)
The reaction between an unfunctionalized conjugated diene and a nitroarene under CO pressure and at 100 °C, catalyzed by [Pd(Phen)2][BF4]2 (Phen = 1,10-phenanthroline), affords the corresponding hetero-Diels -Alder adduct (oxazine) in up to 91% yields in one pot. If the reaction mixture is then heated to 200 °C, the oxazines are converted into the corresponding N-arylpyrroles in good yields. Pressures as low as 5 bar can be employed, and 0.08% catalyst is sufficient to effect the transformation. The reaction can be equally run by employing the nitroarene or the diene as limiting agent and works well for nitroarenes bearing either electron-withdrawing or mildly electron-donating substituents. A moderate steric hindrance on the nitroarene (o-methyl) is well tolerated, but 1,4-disubstituted-1,3-dienes are not suitable substrates.
