含窒素共役系の反応(第3報) : 共役Schiff Baseとジフェニルケテンとの反応
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概要
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The adduct obtained from the reaction of diphenyl ketene (IIa) with the conjugated Schiff base, diacetyl dianil (I), is not a pyrazine derivative (IIIa) as proposed by Pfleger et al., ^<8)> but is 1,3,3-triphenyl-4-methyl-4-(1-anilidene ethyl)-2-azetidinone (Va), whose catalytic reduction gave 1,3,3-triphenyl-4-methyl-4-(1-anilinoethyl)-2-azetidinone (VIa). Similarly, the reaction of I with phenyl ketene (IIb) afforded 1,3-diphenyl-4-methyl-4-(1-anilidene ethyl)-2-azetidinone (Vb). The evidence for this structure assignment is described. Further, reaction between six kinds of conjugated Schiff base with IIa was carried out, and four of these, i.e., N-(9-phenanthridinyl)-methylene phenethylamine (VII), bis (4-methoxyanilino) glyoxal (IX), 2,3-diphenyl-5,6-dihydropyrazine (XI), and cinnamylidene aniline (XIII), afforded the corresponding azetidinone derivatives (VIII, X, XII, and XIVa). On the other hand, isoquinoline derivatives (XVI and XVIII) gave the Michael- type adducts (XVII and XIX).
- 社団法人日本薬学会の論文
- 1970-11-25
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