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Communication | Regular issue | Vol 14, No. 5, 1980, pp.593-598
Published online, 1st January, 1970
DOI: 10.3987/R-1980-05-0593
Synthesis of 4,11-Dimethyl-2,3,4,5-tetrahydro-2,5-iminomethano-6H-benzo[a][1,4,6]thiadiazocine-3,12-decane and 7,9-Dimethyl-8,10-dioxo-2,5-dithia-7,9-diazabicyclo[4.2.2]decane

Taisei Ueda, Noriyuki Sawaki, Noriichi Oda, and Isoo Ito*

*Faculty of Pharmaceutical Sciences, Nagoya City University, Tanabe-dori, Mizuho-ku, Nagoya 467-8603, Japan


Two novel heterocyclic ring systems involving the piprazine ring and the benzothiadiazocine or dithiadiazabicyclodecane skeleton were synthesized : The reaction of 3,6-dibromo-1,4-dimethyl-2,5-piperazinedione (I) with an equivalent mole of o-aminothiophenol in ethanol in the presence of sodim ethoxide or in pyridine gave 4,11-dimethyl-2,3,4,5-tetrahydro-2,5-iminomethano-6H-benzo[a][1,4,6]thiadiazocine-3,12-decane (IIA), while the reaction of I with two moles of o-aminothiophenol gave 3,6-bis(2-aminophenyl)-thio-1,4-dimethyl-2,5-piperazinedione (IIIa). The reaction of I with an equivalent mole of ethanedithiol in ethanol in the presence of sodium ethoxide gave 7,9-diazabicyclo[4.2.2]decane (IV), which was also synthesized from 3,6-dihydroxy-1,4-dimethyl-2,5-piperazinedione (V) and ethanedithiol in dioxane in the presence of zinc chloride.