Synthesis of tetrazole analogs of gamma- and delta-amino acids. |
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Authors: | Panagiota Moutevelis-Minakakis Maria Filippakou Charalambos Sinanoglou George Kokotos |
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Affiliation: | Laboratory of Organic Chemistry, Department of Chemistry, University of Athens, Panepistimiopolis 15784, Greece. pminakak@chem.uoa.gr |
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Abstract: | N-benzyloxycarbonyl-protected alpha- or beta-amino alcohols, easily prepared from alpha- and beta-amino acids, were converted into aldehydes and directly reacted with (triphenyl phosphoranylidene) acetonitrile, leading to unsaturated nitriles. Treatment of nitriles with NaN(3) and ZnBr(2) produced unsaturated gamma- and delta-amino tetrazoles, which were deprotected and converted to the corresponding saturated compounds by catalytic hydrogenation. For the case of delta-amino tetrazole, the methylation of the acidic moiety occurred after treatment with CH(2)N(2), leading to the N(1)- and N(2)-methylated constitutional isomers, which were separated by column chromatography and hydrogenated. |
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Keywords: | γ‐amino acids δ‐amino acids tetrazoles |
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