Synthesis of tetrazole analogs of gamma- and delta-amino acids.
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.
Moutevelis-Minakakis
Panagiota
P
Laboratory of Organic Chemistry, Department of Chemistry, University of Athens, Panepistimiopolis 15784, Greece. pminakak@chem.uoa.gr
Filippakou
Maria
M
Sinanoglou
Charalambos
C
Kokotos
George
G
D000447:Aldehydes / Q000138:chemical synthesis / Q000737:chemistry; D000596:Amino Acids / Q000138:chemical synthesis* / Q000737:chemistry; D000605:Amino Alcohols / Q000138:chemical synthesis / Q000737:chemistry; D002853:Chromatography, Liquid / Q000379:methods; D006865:Hydrogenation; D008956:Models, Chemical; D015394:Molecular Structure; D009570:Nitriles / Q000138:chemical synthesis / Q000737:chemistry; D013237:Stereoisomerism; D013777:Tetrazoles / Q000138:chemical synthesis* / Q000737:chemistry
D000447:Aldehydes; D000596:Amino Acids; D000605:Amino Alcohols; D009570:Nitriles; D013777:Tetrazoles; C045574:1H-tetrazole