Keteneおよびその誘導体の研究(第21報) : Diketeneと亜硝酸ならびに亜硝酸エステルとの反応

抄録

Pyruvaldehyde osazone (IV) was afforded when diketene was treated with sodium nitrite in glacial acetica acid, followed by the addition of phenylhydrazine. When this reaction was taken place in EtOH, ethyl 2-hydroxyiminoacetoacetate (I) was obtained. On the other hand, when diketene was reacted with either amyl or ethyl nitrite in ether with bubbling HCl gas, either amyl 2-hydroxyiminoacetoacetate (V) or (I) was afforded in a better yield (60%). When I was subjected further to the catalytic reduction with Pd-C in ethanolic hydrochloric acid, ethyl 2-aminoacetoacetate hydrochloride (VII) was obtained quantitatively, and when it was reduced further catalytically with Pt-C in water, a compound which corresponds to 2-amino-3-hydroxybutylic acid (II) was obtained quantitatively.