79379-48-9

Upstream product

• 29441-71-2 7a-morpholin-4-yl-3-phenyl-4,4a,5,6,7,7a-hexahydro-cyclopenta[e][1,2]oxazine 
• 36771-30-9 4-cyclopentylidene-3-phenylisoxazol-5(4H)-one 
• 1076-59-1 3-phenyl-4H-isoxazol-5-one 
• 1310823-58-5 (E)-1-phenyl-2-(2-(1-phenylethylidene)cyclopentyl)ethanone 
• 14181-72-7 2-bromo-1-phenyl-ethanone oxime 
• 936-52-7 1-(N-morpholino)cyclopent-1-ene 
• 120-92-3 cyclopentanone 
• 124462-58-4 4,4a,5,6,7,7a-hexahydro-3-phenyl-7a-(trimethylsiloxy)cyclopent-1,2-oxazine 
• 54669-76-0 2-phenacylcyclopentanone 

Relevant academic research and scientific papers

Synthetic method of gold catalytic polysubstituted pyrrole

The invention relates to a synthetic method of 1,2,5-tri-substituted 1,4,5,6-tetrahydro-cyclopentane[b]pyrrole compound. A generation reaction formula is shown as follows (referring to the specification). An o-dihydroxy alkyne compound and organic primary

An Au(i)-catalyzed rearrangement/cyclization cascade toward the synthesis of 2-substituted-1,4,5,6-tetrahydrocyclopenta[b]pyrrole

An Au(i)-catalyzed tandem reaction for the synthesis of 2-phenyl-1,4,5,6-tetrahydrocyclopenta[b]pyrrole derivatives from 1-(1-hydroxy-3-phenylprop-2-yn-1-yl)cyclobutanol and primary amines or NH4OAc has been developed to afford a series of poly

Enone-alkyne reductive coupling: A versatile entry to substituted pyrroles

The reductive coupling of enones or enals with alkynes, followed by olefin oxidative cleavage and Paal-Knorr cyclization, provides a versatile entry to a variety of pyrrole frameworks. A number of limitations of alternate entries to the requisite 1,4-dica

Synthesis of Pyrrole Derivatives from 5,6-Dihydro-4H-1,2-oxazines via Reductive Deoxygenation by Use of Fe3(CO)12

α-Bromooximes such as α-bromoacetophenone oxime and ethyl 3-bromo-2-(hydroxyimino)propanoate react with enamines to give 5,6-dihydro-4H-1,2-oxazines in good yields.Dihydro-1,2-oxazine derivatives are also obtained by the reaction of α-bromooximes with vinyl ethers and silyl enol ethers in the presence of Na2CO3.Dihydro-1,2-oxazines can be converted into pyrrole derivatives via reductive deoxygenation by treating with Fe3(CO)12 in moderate to excellent yields.Iron carbonyl complexes other than Fe3(CO)12 are also effective for the pyrrole-forming reaction.The efficiency of the complexes for this reaction decreases in the or der: Fe3(CO)12 >> Et3NH > Fe2(CO)9 >> Fe(CO)5.Both of the dihydro-1,2-oxazine- and pyrrole-forming reactions can be carried out in a single flask, giving pyrrole derivatives in good yields.

Transition Metal- and Acid-Induced Transformations of 6-Siloxy-Substituted 5,6-Dihydro-4H-1,2-oxazines: Preparation of Pyrroles, Nitrones, 1,4-Dicarbonyl Compounds and Derivatives Thereof

A variety of 6-siloxy-substituted 5,6-dihydro-4H-1,2-oxazines (abbreviation: 1,2-oxazines) 1, 3 could be transformed into di- and trisubstituted pyrroles 2, 4 by means of molybdenum hexacarbonyl.The mechanism of this deoxygenating ring contraction is discussed.With two bicyclic 1,2-oxazines an acid-catalyzed fragmentation affording α-methylenecycloalkanones 7 has been observed, while other 1,2-oxazines rearrange in methanolic acid to give nitrones 9, 10.The desilylation of 6-siloxy-substituted 1,2-oxazines 1.3 employing NEt3*3HF is a very general and smooth process providing 6-hydroxy-1,2-oxazines 11, 12 or their corresponding acyclic tautomers 13, 14 in high yields.For two examples of 11 deoximations by use of formalin could be achieved with moderate efficiency giving 1,4-dicarbonyl compounds 15.

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.

SYNTHESIS OF PYRROLE DERIVATIVES VIA DEOXYGENATION OF 4H-1,2-OXAZINES BY IRON CARBONYLS

The reaction of 5,6-dihydro-4H-1,2-oxazines, which are derived from α-bromooximes and enamines, with iron carbonyl complexes such as Fe3(CO)12 and (C2H5)3NH gives pyrrole derivatives in high yields, accompaning deoxygenation from the oxazines.