Abstract:
Dehydroabietylamine, the starting material, reacted with trifluoroacetic anhydride and acetic anhydride to protect amino group, then converted to ketones:N-trifluoroacetyldehydroabietylamine-7-one(2a) and N-acetyldehydroabietylamine-7-one(2b) by oxidation on ring-B with chromic, the obtained ketones were treated with semicarbazide hydrochloride to afford semicarbazones:N-trifluoroacetyldehydroabietylamine-7-one semicarbazone(3a) and N-acetyldehydroabietylamine-7-one semicarbazone (3b).Compounds 3a and 3b were transformed into ring-B fused 1, 2, 3-thiadiazole derivatives:N-trifluoroacetyldehydroabietylamine-6-ene7, 6-d-1, 2, 3-thiadiazole(4a) and N-acetyldehydroabietylamine-6-ene7, 6-d-1, 2, 3-thiadiazole(4b) by Hurd-Mori reaction with thionyl chloride.Finally, the amide were hydrolysised under alkaline condition to remove protecting groups, and gave dehydroabietylamine-6-ene7, 6-d-1, 2, 3-thiadiazole(5).The structures of three new synthesized dehydroabietylamine 1, 2, 3-thiadiazole derivatives 4a, 4b and 5 were characterized by FT-IR, 1H NMR, 13C NMR and ESI-MS.Their spectrum feature and structure difference were also analyzed.