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Chemistry and Industry of Forest Products ›› 2016, Vol. 36 ›› Issue (1): 141-146.doi: 10.3969/j.issn.0253-2417.2016.01.020

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Synthesis and Structural Characterization of Novel Dehydroabietylamine1, 2, 3-Thiadiazole Derivatives

YU Xing, ZHU Miao-miao, ZHAO Li, LIN Zhong-xiang   

  1. College of Chemical Engineering, Nanjing Forestry University, Nanjing 210037, China
  • Received:2014-11-20 Online:2016-02-25 Published:2016-03-18

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-ene[7, 6-d]-1, 2, 3-thiadiazole(4a) and N-acetyldehydroabietylamine-6-ene[7, 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-ene[7, 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.

Key words: dehydroabietylamine, Hurd-Mori reaction, 1,2,3-thiadiazole, characterization

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