Reaction of methyl 1-bromocyclopentanecarboxylate with zinc and 1-aryl-5-phenylpenta-1,4-dien-3-ones

Methyl 1-bromocyclopentanecarboxylate reacted with zinc and 1-aryl-5-phenylpenta-1,4-dien-3-ones with the formation of isomeric 10-aryl-8-(2-arylethenyl)-7-oxaspiro[4.5]dec-8-en-6-ones.     

Synthesis of 5-amino-1,5-diarylpenta-2,4-dien-1-ones

Nucleophilic addition of morpholine and piperidine to 1,5-diarylpent-2-en-4-yn-1-ones involves the triple bond in the latter, regardless of the substituents in the aryl rings, to produce the corresponding (E,E)-5-(morpholin-4-yl or piperidin-1-yl)-1,5-diarylpenta-2,4-dien-1-ones in up to 93% yield. According to the X-ray diffraction data, the synthesized compounds in crystal have s-cis and s-trans conformations of the enone and dienone fragments, respectively.     

Reaction of substituted chalcones with methyl 1-bromocycloalkanecarboxylates and zinc

Methyl 1-bromocyclopentane-and 1-bromocyclobutanecarboxylates react with zinc and substituted chalcones to form spiro-3,4-dihydropyran-2-one derivatives: 8, 10-diaryl-7-oxaspiro[4.5]dec-8-en-6-ones and 7,9-diaryl-6-oxaspiro[3.5]non-7-en-5-ones, respectively.     

Reaction of methyl 1-bromocycloalkanecarboxylates with zinc and 2,6-bis(arylmethylene)cyclohexanones

Methyl 1-bromocyclopentane-, 1-bromocyclohexane-, and 1-bromocycloheptanecarboxylates react with zinc and 2,6-bis(arylmethylene)cyclohexanones to afford 4-aryl-8-(arylmethylene)-5,6,7,8-tetrahydrospiro[chromene-3,1′-cyclopentan]-2(4H)-ones, 4-aryl-8-(arylmethylene)-5,6,7,8-tetrahydrospiro[chromene-3,1′-cyclohexan]-2(4H)-ones, and 4-aryl-8-(arylmethylene)-5,6,7,8-tetrahydrospiro[chromene-3,1′-cycloheptan]-2(4H)-ones, respectively.     

Reaction of methyl 1-bromocycloalkanecarboxylates with zinc and ethyl 5-aryl-3-oxo-2,2-diethylpent-4-enoates

Methyl 1-bromoalkanecarboxylates react with zinc and ethyl 5-aryl-3-oxo-2,2-diethylpent-4-enoates to form ethyl 2-(10-aryl-6-oxo-7-oxaspiro[4.5]dec-8-en-8-yl)-2-ethylbutanoates and ethyl 2-(5-aryl-1-oxo-2-oxaspiro[5.5]undec-3-en-3-yl)-2-ethylbutanoates.     

Thallium in organic synthesis preparation of steroidal 1,4-dien-3-ones

Steroidal 1,4-dien-3-ones are obtained as major products of the reaction between thallium (III) acetate and Δ¹ or Δ⁴-3-keto steroids in acetic acid. 5α-cholestan-3-one, similarly treated, followed by esterification, gives mainly 2α-carbomethoxy-A-nor-5α-cholestane.     

Reaction of 1,5-Diphenyl-1,4-pentadien-3-one and 1,5-Diphenyl- 1-penten-4-yn-3-one with Monosubstituted Hydrazines

Phenyl- and isopropylhydrazines react with 1,5-diphenyl-1,4-pentadien-3-one to give 4,5,6,7-tetrahydroindazole derivatives instead of the expected 4,5-dihydropyrazoles. The reaction of phenylhydrazine with 1,5-diphenyl-1-penten-4-yn-3-one leads to formation of 1,5-diphenyl-3-phenylethynyl-4,5-dihydropyrazole. 2,4-Dinitrophenylhydrazine reacts with 1,5-diphenyl-1-penten-4-yn-3-one, affording the corresponding unsaturated hydrazone rather than pyrazole derivative.     

Ultrasound-Promoted Synthesis of 1,5-Diarylpenta-2,4-dien-1-ones Catalyzed by Activated Barium Hydroxide

1,5-Diarylpenta-2,4-dien-1-ones were synthesized with ultrasound irradiation in the presence of activated barium hydroxide as catalyst. Compared to conventional methods, the present methodology offers several advantages such as excellent yields, simple procedure, short reaction times, and milder conditions.     

超声波和无溶剂条件下1-芳基-5-二茂铁基-1,4-二烯-3-酮的合成

在室温下使用超声波或无溶剂条件下,4-二茂铁基-3-烯-2-酮和芳香醛的羟醛缩合能以83％～97％的收率得到1-芳基-5-二茂铁基-1,4-二烯3-酮。这种方法具有操作简单,反应条件温和,产率高和低能耗等优点。     

Reaction of 4-methyl-4-tribromomethylcyclohexa-2,5-dien-1-one with zinc metal

4-Methyl-4-tribromomethylcyclohexa-2,5-dien-1-one reacts with zinc dust in absolute DMF to give a mixture of 4-bromo-5-methylcyclohepta-2,4,6-trien-1-one, 4-methyl-cyclohepta-2,4,6-trien-1-one, and 4-dibromomethyl-4-methylcyclohexa-2,5-dien-1-one. Translated fromIzvestiya Akademii Nauk. Seriya Khimicheskaya, No. 1, pp. 177–178, January, 1998.     

Reaction of methyl 1-bromocyclohexanecarboxylate with zinc and 3-aryl-2-cyanopropenoic acids amides

Methyl 1-bromocyclohexanecarboxylate reacts with zinc and amides or methylamides of 3-aryl-2-cyanopropenoic acids to give 5-aryl-1,3-dioxo-2-azaspiro[5.5]undecane-4-carbonitriles or 5-aryl-2-methyl-1,3-dioxo-2-azaspiro[5.5]undecane-4-carbonitriles.     

Reaction of methyl 1-bromocyclopentane-1-carboxylate with zinc and 3-aryl-2-cyanoprop-2-enamides

Reformatsky reaction of methyl 1-bromocyclopentane-1-carboxylic acid with 3-aryl-2-cyanoprop-2-enamides and their N-methyl derivatives afforded 10-aryl-6,8-dioxo-7-azaspiro[4.5]decane-9-carbonitriles and 10-aryl-7-methyl-6,8-dioxo-7-azaspiro[4.5]decane-9-carbonitriles, respectively.     

Reaction of methyl 1-(2-bromo-4-methoxy-1,4-dioxobutyl)- cyclohexanecarboxylate with zinc and aromatic aldehydes

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Reaction of substituted 1,2,8,9-tetraazadispiro[4.1.4.3]tetradeca-1,8-dien-6-ones and 1,2,8,9-tetraazadispiro[4.1.4.2]trideca-1,8-dien-6-ones with chlorine

Reaction of 4,11-diaryl-1,2,8,9-tetraazadispiro[4.1.4.3]tetradeca-1,8-dien-6-ones and-dispiro[4.1.4.2]trideca-1,8-dien-6-ones with chlorine gives substituted dispirocyclic compounds containing a 3-chloro-1-pyrazoline fragment which loses nitrogen on heating to give spirocyclic chlorocyclopropanes. __________ Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 4, pp. 558–566, April, 2008.     

Double C-H activation during functionalization of phenyl(methyl)ketene on iridium(I) using alkynes. synthesis of 1,4-dien-3-ones

Under the influence of an Ir(I) metal fragment, the methyl group of phenyl(methyl)ketene undergoes two C-H activations in reacting with internal alkynes, giving metallacycles 3 in 86-94% yield. Treatment of 3 with CO liberates 1,4-dien-3-ones 5 in 81-93% yield, along with CO complex 4. A possible mechanism for the very selective double C-H activation-alkyne coupling is discussed.     

Reaction of 5-Aryl-4-hetaroyl-3-hydroxy-1-hydroxyethyl-1,5-dihydro-2H-pyrrol-2-ones with Nucleophilic Agents

Russian Journal of General Chemistry - The reaction of 5-aryl-4-hetaroyl-3-hydroxy-1-hydroxyethyl-1,5-dihydro-2H-pyrrol-2-ones with p-toluidine proceeds at the carbonyl group in the side chain at...     

Reaction of zinc enolates derived from 1-aryl-2,2-dibromoalkan-1-ones with 2-arylmethylidenemalononitriles

Zinc enolates derived from 1-aryl-2,2-dibromoalkan-1-ones react with 2-arylmethylidenemalononitriles to give 2-alkyl-3-aryl-2-aroylcyclopropane-1,1-dicarbonitriles.     

Reaction of methyl bromocycloalkanecarboxylates with zinc and dihydroisoquinoline derivative

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