1,721,183 research outputs found

    Synthesis of Protected (1-Phenyl-1H-pyrrol-2-yl)-alkane-1-amines from Phenylnitroso Diels?Alder Adducts with 1,2-Dihydropyridines

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    The reductive cleavage of nitrosobenzene-derived cycloadducts with appropriately protected 1,2-dihydropyridines allows a novel and simple obtainment of substituted N-[1-(1-phenyl-1H-pyrrol-2-yl)alkylamides. This synthesis can also be carried out in a very simple, mild, and practical one-pot procedure without isolation of the corresponding nitrosobenzene cycloadduct by means of catalytic amounts of CuCl

    Synthesis of 2,7-diazabicyclo[2.2.1]heptenes by N-O bond cleavage of arylnitroso diels-alder 1,2-dihydropyridine cycloadducts

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    The cleavage of the N-O bond of nitrosoarene-derived cycloadducts with 1,2-dihydropyridines gives different products depending on the protecting group of the starting dihydropyridine and reaction conditions. The use of catalytic amounts of CuCl in non-nucleophilic solvents in combination with a N-phenoxycarbonyl-protected nitrosophenyl-derived cycloadduct allowed the unprecedented formation of the 2,7-diazabicycle[2.2.1]heptene scaffold. It was also demonstrated that this novel bicyclic gem-diamine derivative is an isolable intermediate en route to pyrrole derivatives. On the other hand, the corresponding nitrosopyridine-derived cycloadduct showed to be unreactive with copper salts, but the application of different reductive conditions can deliver the corresponding bicyclic gem-diamine derivative or 3-aminotetrahydropyridine also in enantioenriched form. © Georg Thieme Verlag Stuttgart
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