Dioxopyrrolines. XXIX. Solvolytic Behavior of 3-Ethoxycarbonyl-2-phenyl-Δ^2-pyrroline-4,5-diones in Protic Solvents
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概要
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The solvolytic behavior of 3-ethoxycarbonyl-2-phenyl-Δ^2-pyrroline-4,5-diones 7 depends on the N-substituents. On treatment with ethanol or methanol, the NH derivative 7a afforded the corresponding keto ester 9,a product of C_5-lactam carbonyl attack, while the N-alkyl derivatives 7b-d gave the enols 8b-d, products of C_2-attack. Kinetic analysis based on time dependent ultraviolet spectra of 7 in ethanolic solution revealed that the C_2-center of the compound is the most electrophilic and that N-alkylation enhances the C_2-electrophilicity. This increase in the electrophilicity can be rationalized in terms of the restricted rotation of the C_2-phenyl group resulting from N-substitution, which prevents the phenyl-dioxopyrroline conjugation, thus destabilizing the dioxopyrroline form. In the solvolytic reaction of 7 in the presence of potassium hydroxide, the products were dependent on the solvent used. In methanol, 7a-b afforded the enolate 18a-b, while in water the carboxylate 19a-b was formed.
- 公益社団法人日本薬学会の論文
- 1985-01-25
著者
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津田 喜典
Faculty of Pharmaceutical Sciences, Kanazawa University
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津田 喜典
Faculty Of Pharmaceutical Sciences Kanazawa University
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佐野 武弘
Showa College of Pharmaceutical Sciences.
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堀口 よし江
昭和薬大
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津田 喜典
金沢大薬
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堀口 よし江
Showa College of Pharmaceutical Sciences
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佐野 武弘
Showa Pharmaceutical Univ. Tokyo Jpn
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佐野 武弘
Showa College Of Pharmaceutical Sciences
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堀口 よし江
Showa College Of Pharmaceutical Sciences University Of Kanazawa
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