Synthesis of Some 3 (or 5)-Substituted 4-Ethoxycarbonyl-5 (or 3)-(1-hydroxyalkyl)-pyrazoles

Gelin, Suzanne; Chabannet, Michel

doi:10.1055/s-1978-24777

Cited by 10 publications

(3 citation statements)

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“…Previously, analogous reactions have been reported with hydrazines and the corresponding open chain compounds [16,17]. Previously, analogous reactions have been reported with hydrazines and the corresponding open chain compounds [16,17].…”

Section: Resultsmentioning

confidence: 69%

REACTIONS OF Β-Tricarbonyl COMPOUND WITH SOME AROMATIC HYDRAZINES AND AMINO ACIDS-ESTERS

Saçmacı¹,

Alkan²

2007

Heterocyclic Communications

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Methyl 2-(4-methoxybenzoyl)-3-(4-methoxyphenyl)-3-oxopropanoylcarbamate 1 which is a new ß-tricarbonyl compound reacted with some aromatic hydrazines 2a-f and amino acids-esters 5a-d to give oxopropanohydrazides 3a-b and pyrazolones 4c-f the together with oxopropanoyl-amino acids-esters 6a-d. These new compounds were obtained in moderate to excellent yields (48-78%). The structures of all new synthesized compounds were determined with the 'H and 13 C NMR, IR spectroscopic data and elemental analyses.Most of them were compared with their previously obtained analogues.

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Section: Resultsmentioning

confidence: 69%

REACTIONS OF Β-Tricarbonyl COMPOUND WITH SOME AROMATIC HYDRAZINES AND AMINO ACIDS-ESTERS

Saçmacı¹,

Alkan²

2007

Heterocyclic Communications

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“…34, 43 The furanone 22 was prepared following a modified literature procedure. 34,43 Ethyl acetoacetate (5.01 g, 38.5 mol) was added to a suspension of magnesium ethoxide (6.04 g, 42.3 mol) in anhydrous benzene (9 mL), the mixture was stirred for one hour at room temperature.…”

Section: Ethyl 2-methyl-4-oxo-45-dihydro-3-furancarboxylate (22)mentioning

confidence: 99%

“…34,43 Ethyl acetoacetate (5.01 g, 38.5 mol) was added to a suspension of magnesium ethoxide (6.04 g, 42.3 mol) in anhydrous benzene (9 mL), the mixture was stirred for one hour at room temperature. Anhydrous acetonitrile (9 mL) was added to the reaction mixture and the flask was cooled to -10 °C, followed by the slow addition of α-chloroacetyl chloride (3.32 mL, 38.5 mol), after which the mixture was allowed to warm to room temperature and left to stir for two hours.…”

Section: Ethyl 2-methyl-4-oxo-45-dihydro-3-furancarboxylate (22)mentioning

confidence: 99%

Studies towards a biomimetic synthesis of α-cyclopiazonic acid: synthesis of 5-substituted isoxazole-4-carboxylic esters

Moorthie¹,

McGarrigle²,

Stenson³

et al. 2006

Arkivoc

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An efficient, high yielding synthesis of ethyl 5-hydroxymethyl-3-methylisoxazole-4-carboxylate has been developed, based on a procedure by Gelin which involves reaction of ethyl acetoacetate with chloroacetyl chloride followed by treatment with hydroxylamine hydrochloride. The product of this reaction was then converted into the bromide and reacted with tetrahydrothiophene to give sulfonium salts in up to 71% overall yield (from ethyl acetoacetate). The synthesis is suitable for use with a chiral sulfide and for large-scale use. The synthesis of ethyl 5-formyl-3-methyl-4-isoxazolecarboxylate and the corresponding tosylhydrazone are also reported. These isoxazoles are starting materials for a proposed convergent, biomimetic synthesis of α-cyclopiazonic acid.

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Enantioselective Synthesis of the Cyclopiazonic Acid Family Using Sulfur Ylides

et al. 2018

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Ac onvergent, nine-step (LLS), enantioselective synthesis of a-cyclopiazonic acid and related natural products is reported. The route features a) an enantioselective aziridination of an imine with ac hiral sulfur ylide;b )abioinspired (3+ +2)-cycloaddition of the aziridine onto an alkene;a nd c) installation of the acetyltetramic acid by an unprecedented tandem carbonylative lactamization/NÀOc leavage of ab romoisoxazole.

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Synthesis of Some 3 (or 5)-Substituted 4-Ethoxycarbonyl-5 (or 3)-(1-hydroxyalkyl)-pyrazoles

Cited by 10 publications

References 0 publications

REACTIONS OF Β-Tricarbonyl COMPOUND WITH SOME AROMATIC HYDRAZINES AND AMINO ACIDS-ESTERS

REACTIONS OF Β-Tricarbonyl COMPOUND WITH SOME AROMATIC HYDRAZINES AND AMINO ACIDS-ESTERS

Studies towards a biomimetic synthesis of α-cyclopiazonic acid: synthesis of 5-substituted isoxazole-4-carboxylic esters

Enantioselective Synthesis of the Cyclopiazonic Acid Family Using Sulfur Ylides

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