Reactions of Enamino Ketones and an Enamino Ester with Some Electrophiles
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概要
- 論文の詳細を見る
Based upon our finding of a novel active site in enamino carbonyl compounds, the details were investigated using some active electrophiles. 1-Phenyl-3-N-pyrrolidinyl-2-buten-1-one (Va) reacted with p-nitrobenzaldehyde in acidic or basic media to afford 1-phenyl-3-N-pyrrolidinyl-5-hydroxy-5-p-nitrophenyl-2-penten-1-one (VI) as the result of IVd-type reaction. The reaction of enamino ketones Va, 4-N-pyrrolidinyl-3-penten-2-one (Vd) and an enamino ester, 1-methoxycarbonyl-2-N-pyrrolidinyl-propene (Vc) with 4-ethoxymethylene-2-phenyl-2-oxazolin-5-one (VIII) gave the corresponding enamino azlactone derivatives (IXa, IXb, IXc), respectively. The reaction of Va and Vb with dichloroketene also afforded IV-d type reaction products, 1,1-dichloro-4-N-pyrrolidinyl-6-phenyl-3-hexene-2,6-dione (XIIa) and 1,1-dichloro-4-N-pyrrolidinyl-3-heptene-2,6-dione (XIIb), respectively. But Vc reacted with dichloroketene to give the ordinary IVb type reaction product. Methanesulfonyl chloride reacted with Vb to yield the cyclic sulfone XIV, which would be produced via sulfonylated intermediate XVII as the result of IVd-type reaction.
- 公益社団法人日本薬学会の論文
- 1970-12-25
著者
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吉本 昌文
Central Research Laboratories, Sankyo Co., Ltd.
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岸田 有吉
Central Research Laboratories Sankyo Co. Ltd.
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平岡 哲夫
New Lead Research Laboratories, Sankyo Co., Ltd.,
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平岡 哲夫
Central Research Laboratories, Sankyo Co., Ltd.
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吉本 昌文
Department Of Chemistry Pomona College
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平岡 哲夫
New Lead Research Laboratories Sankyo Co. Ltd.
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