Condensationsproducte aus Acetondicarbonsäureester und Orthoameisensäureester

Errera, G.

doi:10.1002/cber.18980310263

Cited by 29 publications

(4 citation statements)

References 3 publications

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“…Pyridine-2,4-diol was not formed in our hands by the fusion of 4-hydroxypyridine in a NaOH melt (van Schickh et al, 1936). Synthesis was eventually accomplished via a cyclization procedure (Errera, 1898;den Hertog, 1946).…”

Section: Materials Chemicals and Chemical Synthesesmentioning

confidence: 99%

Microbial metabolism of the pyridine ring. Formation of pyridinediols (dihydroxypyridines) as intermediates in the degradation of pyridine compounds by micro-organisms

Houghton

Cain

1972

Biochemical Journal

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1. Several species of micro-organisms that were capable of utilizing pyridine compounds as carbon and energy source were isolated from soil and sewage. Compounds degraded included pyridine and the three isomeric hydroxypyridines. 2. Suitable modifications of the cultural conditions led to the accumulation of pyridinediols (dihydroxypyridines), which were isolated and characterized. 3. Three species of Achromobacter produced pyridine-2,5-diol from 2- or 3-hydroxypyridine whereas an uncommon Agrobacterium sp. (N.C.I.B. 10413) produced pyridine-3,4-diol from 4-hydroxypyridine. 4. On the basis of chemical isolation, induction of the necessary enzymes in washed suspensions and the substrate specificity exhibited by the isolated bacteria, the initial transformations proposed are: 2-hydroxypyridine --> pyridine-2,5-diol; 3-hydroxypyridine --> pyridine-2,5-diol and 4-hydroxypyridine --> pyridine-3,4-diol. 5. A selected pyridine-utilizer, Nocardia Z1, did not produce any detectable hydroxy derivative from pyridine, but carried out a slow oxidation of 3-hydroxypyridine to pyridine-2,3-diol and pyridine-3,4-diol. These diols were not further metabolized. 6. Addition of the isomeric hydroxypyridines to a model hydroxylating system resulted in the formation of those diols predicted by theory.

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Section: Materials Chemicals and Chemical Synthesesmentioning

confidence: 99%

Microbial metabolism of the pyridine ring. Formation of pyridinediols (dihydroxypyridines) as intermediates in the degradation of pyridine compounds by micro-organisms

Houghton

Cain

1972

Biochemical Journal

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“…Stage 2. This reaction was first described by Errera (albeit mainly directed towards the 4-isomer) and results exclusively in the formation of one pyridone isomer. The literature procedure for stage 2 14 involves reaction of 17 with ethyl malonate monoamide, malonamide, or cyanoacetamide and sodium ethoxide in ethanol.…”

Section: Discussionmentioning

confidence: 96%

6-(Trifluoromethyl)pyrid-2-one: Development and Scale-Up of a Ring Synthesis Route Based on Trifluoroacetic Anhydride

Brown

Bowden

Parsons

et al. 1997

Org. Process Res. Dev.

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Three routes to 6-(trifluoromethyl)pyrid-2-one involving de noWo synthesis of the pyridine ring have been investigated which would potentially allow rapid semi-technical scale manufacture. A route starting from ethyl 4,4,4-trifluoroacetoacetate (β-keto ester route) has been demonstrated. Development of the route was attempted; however, poor yields at a number of stages and scale-up difficulties made this route unattractive for commercial use. A four-stage route starting from trifluoroacetic anhydride and an alkyl vinyl ether (TFAA route) has been developed which gives good yields and productivity for all stages. The final stage of this route is a difficult decarboxylation of a nicotinic acid derivative, but an 80% yield of the required pyridone with a purity of >99.5% could be achieved without a separate purification stage. The route was scaled up to 2000 L, and several hundred kilograms of product was prepared.

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“…With dry ice bath cooling, concentrated NH4OH was added until the pH of the solution was maintained at 6.5. The precipitated crystalline product was collected on a filter and recrystallized from EtOAc to give 1.2 g (90%) of 7: mp 145 °C; ymM 3160, 2160, 1715 cm"1; NMR (Me2SO-d6) 3.74 (s, 3 6-Aminopyrazolo[4,3-c]pyridin-4(5//)-one (2). A mixture of 20 ml of anhydrous NH;i and 550 mg (3.3 mmol) of 7 was heated 90 h in a steel bomb at 110 °C.…”

Section: Methyl 3-(carbamoyimethyi)pyrazole-4-carboxylate (6)mentioning

confidence: 99%

“…Condensation of hydrazine with dimethyl a-ethoxymethylidineacetonedicarboxylate (3) gave the required starting material for the synthetic procedure, methyl 3-(methoxycarbonylmethyl)pyrazole-4-carboxylate (4), albeit in only 6% yield. The major product of this reaction (36%) was found to be the product of cyclization to the ester function, methyl l-amino-4-hydroxypyridin-2-one-5-carboxylate (5).…”

mentioning

confidence: 99%

6-Aminopyrazolo[4,3-c]pyridin-4(5H)-one, a novel analog of guanine

Ehler¹,

Robins²,

Meyer³

1977

J. Med. Chem.

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Treatment of dimethyl alpha-ethoxymethylidineacetonedicarboxylate with hydrazine gave methyl 3-(methoxy-carbonylmethyl)pyrazole-4-carboxylate which, upon ammonolysis and dehydration, afforded methyl 3-(cyanomethyl)pyrazole-4-carboxylate. This compound, when heated with liquid ammonia, gave 6-aminopyrazolo[4,3-c]pyridin-4(5H)-one, a new guanine analogue, which did not possess any of the potent antiviral activity shown by 6-aminoimidazo[4,5-c]pyridin-4(5H)-one (3-deazaguanine).

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Condensationsproducte aus Acetondicarbonsäureester und Orthoameisensäureester

Cited by 29 publications

References 3 publications

Microbial metabolism of the pyridine ring. Formation of pyridinediols (dihydroxypyridines) as intermediates in the degradation of pyridine compounds by micro-organisms

Microbial metabolism of the pyridine ring. Formation of pyridinediols (dihydroxypyridines) as intermediates in the degradation of pyridine compounds by micro-organisms

6-(Trifluoromethyl)pyrid-2-one: Development and Scale-Up of a Ring Synthesis Route Based on Trifluoroacetic Anhydride

6-Aminopyrazolo[4,3-c]pyridin-4(5H)-one, a novel analog of guanine

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