36771-30-9

Upstream product

• 1076-59-1 3-phenyl-4H-isoxazol-5-one 
• 120-92-3 cyclopentanone 
• 36771-31-0 4-cyclopent-1-enyl-3-phenyl-2H-isoxazol-5-one; compound with morpholine (1:1) 
• 94-02-0 ethyl 3-oxo-3-phenylpropionate 
• 936-52-7 1-(N-morpholino)cyclopent-1-ene 

Downstream Products

• 79379-48-9 4,5-dihydro-2-phenylcyclopentapyrrole 
• 120621-43-4 4-Cyclopentyl-3-phenyl-4H-isoxazol-5-one 
• 96151-82-5 4,5-dihydro-2-phenylcyclopentapyrrole-3-carboxylic acid 
• 185845-99-2 1-(5-Oxo-3-phenyl-4,5-dihydro-isoxazol-4-yl)-cyclopentanecarbonitrile 
• 65156-02-7 4-[2-(1-methyl-1H-naphtho[1,2-d]thiazol-2-ylidene)-cyclopentyLiDene]-3-phenyl-4H-isoxazol-5-one 
• 1206892-71-8 1-(5-oxo-3-phenyl-2,5-dihydro-isoxazol-4-yl)-cyclopentanecarboxylic acid tert-butylamide 
• 494844-81-4 4-(1-allyl-cyclopentyl)-3-phenyl-4H-isoxazol-5-one 

Relevant academic research and scientific papers

Michael Addition of Soft Carbon Nucleophiles to Alkylidene Isoxazol-5-ones: A Divergent Entry to β-Branched Carbonyl Compounds

A novel, divergent strategy toward the synthesis of β-branched (and linear) carbonyl compounds is developed by taking advantage of alkylidene isoxazol-5-ones as key building blocks. The yields obtained range from good to excellent, therefore making the described methods attractive options for building such molecules. (Chemical Equation).

Unusual approach to branched 3-alkynylamides and to 1,5-dihydropyrrol-2- ones

[Chemical equation presented] Rare carboxamide branched alkynes such as 11a can be readily obtained by reaction of the electrophilic 4-alkylidene isoxazolinones with isocycanides followed by nitrosative cleavage of the heterocyclic ring. N-lodosuccinimide induced ring closure in the presence of a nucleophile results in the formation of new iodopyrrolinones such as 16c.

A new convergent approach to α-branched alkynes

A variety of α-branched alkynes can be easily assembled by a Knoevenagel type condensation of 4-unsubstituted isoxazolin-5-ones with aldehydes or ketones, followed by conjugate addition of an organometallic reagent and nitrosative cleavage of the heterocy

A convergent approach to functionalised alkynes

Knoevenagel type condensation of 4-unsubstituted isoxazolinones with ketones or aldehydes followed by Michael addition of a nucleophile - hydride, cyanide, or phosphite - and exposure of the adduct to sodium nitrite/aqueous acetic acid and ferrous sulfate

4-Alkylideneisoxazol-5-ones. Synthesis, Tautomerism, and Rearrangement to Pyrroles

The synthesis of several 4-alkylidene- and 4-cycloalkylideneisoxazol-5-ones is described and their tautomerism is investigated by 13C NMR, 1H NMR and IR spectroscopy.Through hydrogen shifts involving the exocyclic substituent (2-propylidene, cyclopentylidene, or 2-indanylidene) these compounds can exist in CH, NH, or OH forms (Scheme II).The CH form is favored in solvents of low polarity (CDCl3) and in the absence of special enthalpic and conjugative effects stabilizing the NH form.The NH form is favored in polar solvents (Me2SO), and its dominance is accentuated when the vinylic substituent is stabilized thermodynamically and conjugationally.The OH form is not observed directly, but the ionized O- form is present in the morpholinium salts of 15, 16, and 17.In the 2-propylidene derivative 12 only the CH form was spectroscopically detectable, but H/D exchange experiments on this and other isoxazolones showed that tautomerism does take place (12 * 24).The alkylideneisoxazolones rearrange to pyrrolecarboxylic acids on flash vacuum pyrolysis.Of two possible mechanisms, a vinylnitrene mechanism (Scheme IV) and a nitrile ylide mechanism (Scheme V), the former is shown to apply.The pyrrolecarboxylic acids often decarboxylate under the reaction conditions.