Products from furans. V Synthesis of oxygen containing isosteres of sympathomimetic amines via 6-hydroxy-2H-pyran-3(6H)-ones and their cis-platinum(II) complexes

Novel amino analogues of sympathomimetic amines, which contain the pyran ring as a consequence of their common route of preparation, were synthesized. A modified Strecker reaction on tetrahydro-2H-pyran-3-one derivatives yielded α-benzylamino nitriles, which upon subsequent hydrogenation and hydrogenolysis gave the target 1,2-diamines. The prepared diamines were indeed sympathomimetic on the basis of molecular mechanics studies, since they have been found to fulfill earlier considerations on the minimal structural requirements, necessary to attain high affinity to dopamine (DA) receptors. Furthermore the prepared 1,2-diamino compounds were used as ligands for the synthesis of cis-Platinum(II) complexes.