Aminoethylation(第1報) : 1-p-Tolylsulfonyl(or Benzylsulfonyl)aziridineとDiethyl MalonateおよびEthyl Acetoacetateとの反応

抄録

1-p-Tolylsulfonyl-or benzylsulfonyl-aziridine (Ia or b) reacted with sodium ethyl malonate in ethanol or benzene to produce ethyl 1-p-tolylsulfonyl-or benzylsulfonyl-2-oxo-3-pyrrolidinecarboxylate (IIa or b). On the other hand, in diethyl carbonate, 2, 7-bis (benzylsulfonyl)-2, 7-diazaspiro [4, 4] nonane-1, 6-dione (VIII) was obtained from Ib. Reaction of Ia and b with sodium ethyl acetoacetate also produced 1-p-tolylsulfonyl-or benzylsulfonyl-3-acetyl-2-pyrrolidinone (XIa or b) but, with sodium ethyl cyanoacetate, the expected products were not obtained. The benzylsulfonyl group in II, VIII, and XI was more easily removed by heating with Raney nickel in ethanol than the p-tolylsulfonyl group to the corresponding pyrrolidinone derivatives.