The Methoxymercuration of N-Allylphthalimide

Pearson, D. E.; Sigal, Max V.; Krug, Roxanne

doi:10.1021/jo01151a022

Cited by 7 publications

(3 citation statements)

References 8 publications

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“…Found: C, 41.9; H, 3.85; N, 3.93; CH30 , 8.64. Pearson, Sigal, and Krug (6) recorded m.p. 108-109°( corr.).…”

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confidence: 98%

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An ANTIMALARIAL ALKALOID FROM HYDRANGEA. VII. 3-[Β-Keto-Γ-(5-Hydroxy-2-Piperidyl)propyl]-4-Quinazolone, AN ISOMER

Baker¹,

Querry²,

Pollikoff³

et al. 1952

J. Org. Chem.

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“…Found: C, 41.9; H, 3.85; N, 3.93; CH30 , 8.64. Pearson, Sigal, and Krug (6) recorded m.p. 108-109°( corr.).…”

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confidence: 98%

“…Pearson, Sigal, and Krug(6) have since described the preparation of this compound from allylphthalimide, but not without isolation of the intermediates.…”

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confidence: 99%

An ANTIMALARIAL ALKALOID FROM HYDRANGEA. VII. 3-[Β-Keto-Γ-(5-Hydroxy-2-Piperidyl)propyl]-4-Quinazolone, AN ISOMER

Baker¹,

Querry²,

Pollikoff³

et al. 1952

J. Org. Chem.

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“…Pearson, Sigal, and Krug(10) have recently described the synthesis of this compound, m.p. 61.5-62.5°, by a laborious three-step process from 2-hydroxy-3-methoxypropyl chloride in 44% over-all yield.…”

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confidence: 99%

An ANTIMALARIAL ALKALOID FROM HYDRANGEA. X. SYNTHESIS OF 3-[Β-Keto-Γ-(4-Methyl-2-Pyrrolidyl)propyl]-4-Quinazolone

Baker¹,

Schaub²,

Williams³

1952

J. Org. Chem.

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Two possible structures suggested for the Hydrangea alkaloid contained an hydroxymethylpyrrolidine group in the side chain, one of which was 3-[/3-keto-7-(4-hydroxymethyl-2-pyrrolidyl)propyl]-4-quinazolone (IX, R = OH) (1). It seemed advisable to synthesize the desoxy derivative of this compound (IXa) in order to establish the method employed without the additional complicating factor of the hydroxyl (or methoxyl) group.Application of the modified aminoketone cyclization (2) to the preparation of 1carbethoxy-4-methylpyrrolidine-2-acetic acid (VIII) would require as an intermediate 3-methyl-4-carbobenzoxyaminobutyric acid (Va), for which a number of methods were investigated. Reduction of /3-cyanobutyric acid should give rise to 4-methyl-2-pyrrolidone which could be hydrolyzed to 3-methyl-4-aminobutyric acid. According to Higginbottom and Lapworth (3) treatment of crotonic ester with sodium cyanide leads to the sodium salt of 3-cyanobutyric acid. These authors then hydrolyzed the intermediate cyano acid, without isolation, to methylsuccinic acid. Attempted isolation of this intermediate has now shown that less than 10% of 3-cyanobutyric acid was left in the solution before addition of alkali. That the /3-cyano group is hydrolytically unstable under the conditions of the sodium cyanide reaction is not surprising since /3-cyanopropionic acid has been reported to hydrolyze in water at room temperature at an appreciable rate (4).Curtius degradation of /3-carbomethoxyisobutyryl chloride (IV), prepared in five steps from methyl crotonate (5), by sodium azide and rearrangement in the presence of benzyl alcohol followed by alkaline hydrolysis, gave the desired bu-109 SUMMARY Synthesis of the model compound, 3-[S-keto-y-(4-methyl-2-pyrrolidyl)propyl]-4-quinazolone, starting with either ß-methylglutaric acid or phthalimidoacetone has been described via the key intermediates, 3-methyl-4-carbobenzoxyaminobutyric acid and l-carbethoxy-4-methyl-2-pyrrolidineacetic acid.Pearl River, N. Y.

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Mercurated amides of alpha‐amino acids

Foye

Mode

1955

Journal of the American Pharmaceutical Association (Scientific

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The Methoxymercuration of N-Allylphthalimide

Cited by 7 publications

References 8 publications

An ANTIMALARIAL ALKALOID FROM HYDRANGEA. VII. 3-[Β-Keto-Γ-(5-Hydroxy-2-Piperidyl)propyl]-4-Quinazolone, AN ISOMER

An ANTIMALARIAL ALKALOID FROM HYDRANGEA. VII. 3-[Β-Keto-Γ-(5-Hydroxy-2-Piperidyl)propyl]-4-Quinazolone, AN ISOMER

An ANTIMALARIAL ALKALOID FROM HYDRANGEA. X. SYNTHESIS OF 3-[Β-Keto-Γ-(4-Methyl-2-Pyrrolidyl)propyl]-4-Quinazolone

Mercurated amides of alpha‐amino acids

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