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Note | Regular issue | Vol 51, No. 10, 1999, pp.2453-2462
Published online, 1st January, 1970
DOI: 10.3987/COM-99-8645
A Convenient Synthesis of (Z)-3- (α-Cyano-α-alkoxycarbonylmethylene)-2-piperazinones and Their Derivatives

Yoichi Yamada,* Heinosuke Yasuda, and Masaaki Kasai

*Utsunomiya University, 350 Mine, Utsunomiya 321-8505, Japan


(Z)-3-(α-Cyano-α-alkoxycarbonylmethylene)-2-piperazinone derivatives (3) and trans-(Z)-3-(α-cyano-α-alkoxycarbonylmethylene)-octahydro-2(1H)-quinoxalinone derivatives (5) possessing various alkoxycarbonyl groups are prepared directly from the reaction of dialkyl (E)-2,3-dicyanobutenedioates (1) with ethylenediamine (2) and with trans-1,2-diaminocyclohexane (4), respectively. Furthermore, cis-1,2-diaminocycloheptane (6) and meso-2,3-diaminobutane (8) were reacted with the diethyl ester 1b to give cis-(Z)-3-(α-cyano-α-ethoxycarbonyl-methylene)decahydro-2H-cycloheptapyrazin-2-one (7) and cis-(Z)-3-(α-cyano-α-ethoxycarbonylmethylene)-5,6-dimethyl-2-piperazinone (9), respectively. The structural studies of 3, 5, 7, and 9 were carried out by NMR experiments in some details.