β-Propiolactone. VI. Reactions with Phenols, Thiophenols and their Salts

Gresham, T. L.; Jansen, J. E.; Shaver, F. W.; Bankert, R. A.; Beears, W. L.; Prendergast, Marie G.

doi:10.1021/ja01170a078

Cited by 44 publications

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“…Gresham et al [82] have reported the conversion of 3-cholorophenol 66 to β-phenoxypropionic acid 67 using β-propiolactone under alkaline conditions, which was readily reproduced. Ring-closure of the intermediate 67 was achieved using polyphosphoric acid to afford 55 (Scheme 4).…”

Section: Mechanistic Discussion: Beckmann Rearrangementmentioning

confidence: 95%

The Application of the Schmidt Reaction and Beckmann Rearrangement to the Synthesis of Bicyclic Lactams: Some Mechanistic Considerations

2010

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The syntheses of some methoxy-substituted bicyclic lactams, of the types 3 and 4, are reported employing two different conditions for the Schmidt reaction of appropriate ketones and employing two different conditions for the Beckmann rearrangement of the corresponding ketoximes. The alkyl to aryl migration ratios of the reactions were determined by high-performance liquid chromatography analysis of the reactions. The mechanisms of the reactions reported are discussed, some limitations of the reported mechanisms identified, and an alternative mechanism proposed in light of the outcomes of the various reactions. Application of the Schmidt reaction and Beckmann rearrangement was used for the synthesis of some chloro bicyclic lactams, of the types 3 and 4.

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Section: Mechanistic Discussion: Beckmann Rearrangementmentioning

confidence: 95%

The Application of the Schmidt Reaction and Beckmann Rearrangement to the Synthesis of Bicyclic Lactams: Some Mechanistic Considerations

2010

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“…Auf diese Weise sind z. B. p-Amino oder p-Mercaptocarbonsauren zuganglich [5] [6]. Die Reaktivitat der B-Carbonyl-Position fur den nucleophilen Angriff wird naturgemass durch Substituenten an diesem Zentrum erschwert: wahrend z.…”

Section: -Ethoxy-13-dioxan-4-oneunclassified

“…Offensichtlich behindert der zusatzliche Substituent den nucleophilen Angriff von H,O unter SN2-Reaktion. [6], wahrend ihre Natrium-Salze wesentlich reaktiver sind. Dies beobachteten wir auch bei den Umsetzungen mit (S)-P-Butyrolacton (1).…”

Section: -Ethoxy-13-dioxan-4-oneunclassified

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Herstellung enantiomerenreiner Derivate von 3‐Amino‐ und 3‐Mercaptobuttersäure durch S_N2‐Ringöffnung des β‐Lactons und eines 1,3‐Dixoanons aus der 3‐Hydroxybuttersä ure

Griesbeck

Seebàch²

1987

Helvetica Chimica Acta

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From (S)-4-methyloxetan-2-one (l), the b-butyrolactone readily available from the biopolymer (R)-polyhydroxybutyrate (PHB) and various C,N,O and S nucleophiles, the following compounds are prepared: (S)-2-hydroxy-4-octdnone (3), (R)-3-aminobutanoic acid (7) and its N-benzyl derivative 5, (R)-3-azidobutanoic acid (6), (R)-3-mercaptobutdnoic acid (lo), (R)-3-(phenylthio)butdnoic acid (8) and its sulfoxide 9. The (6R)-2,6-dimethyl-2-ethoxy-1.3-dioxan-4-one (4) from (R)-3-hydroxybutanoic acid undergoes SN2 ring opening with benzylamine to give the N-benzyl derivative (enj-5) of (S)-3-aminobutanoic acid in 3040% yield.Einleitung. -Die Umsetzung des p-Lacton-Grundkorpers (P-Propiolacton) mit verschiedenen Nucleophilen wurde intensiv untersucht und auch in zwei Ubersichtsartikeln zusammengefasst [ 11 [2]. Seit D-Propiolacton kommerziell zuganglich wurde [3], waren es besonders Gresham und Mitarbeiter, die sich urn das Verstiindnis dieser Reaktionen und ihre synthetische Nutzbarmachung bemiihten [4]. Prinzipiell kann ein ,6-Lacton mit einem Reagenz Nu-M auf zwei verschiedene Arten geoffnet werden: in der Reaktion vom Typ I wird die [C(=O)-01-Bindung, in der vom Typ I1 die (Alkyl-0)-Bindung gebro-

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“…In brief, treatment of guaiacol (1) with NaH and 3-bromopropionic acid in DMF gave phenoxypropionic acid 2. [15] This intermediate cyclized in the presence of polyphosphoric acid to chromanone 3.…”

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confidence: 99%

A Benzopyrane Derivative as a P‐Glycoprotein Stimulator: A Potential Agent to Decrease β‐Amyloid Accumulation in Alzheimer’s Disease

et al. 2011

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A simulating interaction: The P‐glycoprotein (P‐gp) ligand 13 displays high P‐gp interacting activity (EC50=2.90 μM) and selectivity in tumor cell lines. Here, this promising compound was further evaluated ex vivo in an everted gut sac assay and found to behave as a P‐gp stimulator, making this agent a potential lead for the development of new therapeutics to treat Alzheimer′s disease.

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β-Propiolactone. VI. Reactions with Phenols, Thiophenols and their Salts

Abstract: temperature to give /3-phenoxypropionic acid (II) and a small amount of a polymer of I.At higher temperatures (above 150°) the poly-merization2 becomes the major reaction. Except

Cited by 44 publications

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The Application of the Schmidt Reaction and Beckmann Rearrangement to the Synthesis of Bicyclic Lactams: Some Mechanistic Considerations

The Application of the Schmidt Reaction and Beckmann Rearrangement to the Synthesis of Bicyclic Lactams: Some Mechanistic Considerations

Herstellung enantiomerenreiner Derivate von 3‐Amino‐ und 3‐Mercaptobuttersäure durch S_N2‐Ringöffnung des β‐Lactons und eines 1,3‐Dixoanons aus der 3‐Hydroxybuttersä ure

A Benzopyrane Derivative as a P‐Glycoprotein Stimulator: A Potential Agent to Decrease β‐Amyloid Accumulation in Alzheimer’s Disease

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β-Propiolactone. VI. Reactions with Phenols, Thiophenols and their Salts

Abstract: temperature to give /3-phenoxypropionic acid (II) and a small amount of a polymer of I.At higher temperatures (above 150°) the poly-merization2 becomes the major reaction. Except

Cited by 44 publications

References 0 publications

The Application of the Schmidt Reaction and Beckmann Rearrangement to the Synthesis of Bicyclic Lactams: Some Mechanistic Considerations

The Application of the Schmidt Reaction and Beckmann Rearrangement to the Synthesis of Bicyclic Lactams: Some Mechanistic Considerations

Herstellung enantiomerenreiner Derivate von 3‐Amino‐ und 3‐Mercaptobuttersäure durch SN2‐Ringöffnung des β‐Lactons und eines 1,3‐Dixoanons aus der 3‐Hydroxybuttersä ure

A Benzopyrane Derivative as a P‐Glycoprotein Stimulator: A Potential Agent to Decrease β‐Amyloid Accumulation in Alzheimer’s Disease

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Herstellung enantiomerenreiner Derivate von 3‐Amino‐ und 3‐Mercaptobuttersäure durch S_N2‐Ringöffnung des β‐Lactons und eines 1,3‐Dixoanons aus der 3‐Hydroxybuttersä ure