Synthesis of new tetrazole and triazole substituted pyroglutamic acid and proline derivatives

Article abstract of DOI:10.1016/j.tetlet.2006.11.163

Racemic 4-(substituted-1H-1,2,3-triazol-1-yl), 4-aryl and 4-(arylmethyl)tetrazolyl-pyroglutamic and proline derivatives were synthesized from dimethyl-2,4-dibromoglutaryle 1 in good yield using mild reaction conditions. The key step for the preparation of the triazole substituted molecule was the 1,3-dipolar cycloaddition of an acetylenic compound with an azido derivative. The tetrazole derivatives were prepared by the selective N2-alkylation of 5-substituted tetrazoles with 1.