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Synthesis 1990; 1990(11): 1020-1023
DOI: 10.1055/s-1990-27081
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Oxidative Heterocyclization Using Diethyl Azodicarboxylate

Yoshito Kihara* , Shigeru Kabashima, Kazue Uno, Tadashi Okawara, Tetsuo Yamasaki, Mitsuru Furukawa
  • *Faculty of Pharmaceutical Sciences, Kumamoto University, Oehon-machi, Kumamoto 862, Japan
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Publication Date:
17 September 2002 (online)

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The reactions of amidinothioureas, imidoylthioureas, thioacylamidines, O-methyl-1-aryl-2-thioisobiurets, and 1-aryl-isodithiobiurets with diethyl azodicarboxylate (DEAD, diethyl diazenedicarboxylate) gave the corresponding thiadiazoles by the oxidative cyclic S-N bond formation. Analogously, the oxidative cyclization of 2-phenyl-5-(1-methylthiosemicarbazido)-3(2H)-pyridazinones with DEAD provided 4-methyl-7-phenyl-4H-pyridazino[4,5-e] [1,3,4]-thiadiazin-8(7H)-ones.