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 and structure of 4,9-diaryl-3a,4,9,9a-tetrahydrospiro-[furo[3,4-f]chromene-8,1’-cyclopentane]-1,3,7(9bH)-triones

Reactions of (E)-10-aryl-8-(2-arylethenyl)-7-oxaspiro[4.5]dec-8-en-6-ones with maleic anhydride result in the formation of 4,9-diaryl-3a,4,9,9a-tetrahydrospiro[furo[3,4-f]chromene-8,1′-cyclopentane]-1,3,7(9bH)-triones whose structure was established by XRD analysis.     

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.     

Reaction of Reformatsky reagent prepared from methyl 1-bromocyclohexanecarboxylate and zinc with substituted chalcones

Methyl 1-bromocyclohexanecarboxylate reacts with zinc and substituted chalcones yielding the corresponding spiro-3,4-dihydropyran-2-one derivatives, 3-aryl-5-aryl-2-oxaspiro[5.5]undec-3-en-1-ones.     

A convenient synthesis of functionalized 8- and 9-aza-1-oxaspiro[5.5]undecanes

2-Hydroxy-8-(or 9-)aza-1-oxaspiro[5.5]undec-3-en-5-ones derived from their corresponding 2-furfuryl alcohols were used as key intermediates for the convenient synthesis of several novel 8- and 9-aza-1-oxaspiro[5.5]undecane derivatives.     

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.     

Synthesis of substituted methyl 5,5-polymethylene-2,4-dioxotetrahydropyran-3-carboxylates

Dimethyl 2-(1-bromocyclohexylcarbonyl)-, 2-(1-bromocyclopentylcarbonyl)-, and 2-(1-bromocyclobutylcarbonyl)-2-methylmalonates reacted with zinc and aromatic aldehydes to give the corresponding methyl 1-aryl-4-methyl-3,5-dioxo-2-oxaspiro[5.5]undecane-4-, 6-aryl-9-methyl-8,10-dioxo-7-oxaspiro[4.5]-decane-9-, and 5-aryl-8-methyl-7,9-dioxo-6-oxaspiro[3.5]nonane-8-carboxylates.     

Chelation-control in the formal [3+3] cyclization of 1,3-bis-(silyloxy)-1,3-butadienes with 1-hydroxy-5-silyloxy-hex-4-en-3-ones. One-pot synthesis of 3-aryl-3,4-dihydroisocoumarins

The [3+3] cyclization of 1,3-bis(silyloxy)-1,3-butadienes with 1-hydroxy-5-silyloxy-hex-4-en-3-ones resulted in the one-pot formation of 3-aryl-3,4-dihydroisocoumarins. The reactions proceeded by regioselective cyclization to give 6-(2-aryl-2-chloroethyl)salicylates, which underwent a silica gel-mediated lactonization. The cyclizations of protected 1-amino-5-silyloxy-hex-4-en-3-ones proved to be not regioselective.     

Regioselective synthesis of amino- and nitroarenes based on [3+3] cyclocondensations of 1,3-bis(silyloxy)-1,3-butadienes

Functionalized amino- and nitro-substituted biaryls and dibenzo[b,d]pyrid-6-ones (6(5H)-phenanthridinones) were prepared by [3+3]cyclocondensation of 1,3-bis(trimethylsilyloxy)-1,3-butadienes with nitro-substituted 1-aryl-1-silyloxy-1-en-3-ones and subsequent hydrogenation. 4-Nitro- and 4-aminophenols were prepared based on formal [3+3] cyclizations of 1,3-bis(trimethylsilyloxy)-1,3-butadienes with 3-ethoxy-2-nitro-2-en-1-ones.     

Synthesis of 3-aryl-3,4-dihydroisocoumarins by regioselective domino ‘[3+3] cyclization/lactonization’ reactions of 1,3-bis-(silyloxy)-1,3-butadienes with 1-hydroxy-5-silyloxy-4-en-3-ones

The [3+3] cyclization of 1,3-bis(silyloxy)-1,3-butadienes with 1-hydroxy-5-silyloxy-4-en-3-ones afforded 6-(2-aryl-2-chloroethyl)salicylates, which were transformed into 3-aryl-3,4-dihydroisocoumarins by silica gel-mediated lactonization.     

Reaction of Methyl 1-(2-Bromoisobutyryl)cyclopentane-carboxylate and 3-(1-Bromocyclopentyl)-2,2-dimethyl-3-oxo-propionate with Zinc and Aromatic Aldehydes

Methyl 1-(2-bromoisobutyryl)cyclopentanecarboxylate and 3-(1-bromocyclopentyl)-2,2-dimethyl-3-oxopropionate react with zinc and aromatic aldehydes to afford 8-aryl-9,9-dimethyl-7-oxaspiro[4.5]decane-6,10-diones and 10-aryl-7,7-dimethyl-9-oxaspiro[4.5]decane-6,8-diones, respectively.     

Synthesis of 6-aryltetrahydropyran-2,4-diones containing a hexamethylene substituent in positions 3 or 5 of heterocycle

Methyl 3-(1-bromocycloheptyl)-2,2-dimethyl-3-oxopropanoate and methyl 1-(2-bromo-2-methylpropanoyl)cycloheptanecarboxylates react with zinc and arylcarbaldehydes yielding 5-aryl-2,2-dimethyl-4-oxaspiro[5.6]dodecan-1.3-diones and 3-aryl-4,4-dimethyl-2-oxaspiro[5.6]dodecan-1.5-diones respectively.     

Multicomponent reaction of conjugated enynones with malononitrile and sodium alkoxides: Complex reaction mechanism of the formation of pyridine derivatives

Reaction of conjugated enynones,1,5-diarylpent-2-en-4-yn-1-ones, with malononitrile and sodium alkoxides in the corresponding alcohols at room temperature for 3–23 h results in the formation of two types of compounds (E)-/(Z)-6-aryl-4-(2-arylethenyl)-2-alkoxypyridine-3-carbonitriles (substituted nicotinonitriles), as the major reaction products in yields up to ca. 40–80%, and 6-aryl-4-arylethynyl-2-alkoxypyridines, as the minor reaction products in yields of 5–17%. Plausible mechanism of this complex and multistep reaction is discussed. The obtained pyridines possess fluorescent properties.     

First synthesis of functionalized 5-aryl-3-(trifluoromethyl)phenols by regioselective [3+3] cyclocondensations of 1,3-bis(silyloxy)-1,3-butadienes with 3-aryl-3-silyloxy-1-trifluoromethyl-2-en-1-ones

A variety of functionalized 5-aryl-3-(trifluoromethyl)phenols were prepared by the first TiCl₄-mediated [3+3] cyclocondensation of 1,3-bis(trimethylsilyloxy)-1,3-butadienes with 3-aryl-3-trimethylsilyloxy-1-trifluoromethyl-2-en-1-ones.     

Five-membered 2,3-dioxo heterocycles: LXXXIX. Reaction of methyl 1-aryl-3-cinnamoyl-4,5-dioxo-4,5-dihydro-1H-pyrrole-2-carboxylates with (E)-4-arylaminopent-3-en-2-ones. Crystalline and molecular structure of 9-acetyl-4-cinnamoyl-3-hydroxy-1-(4-methoxyphenyl)-8-methyl-7-phenyl-1,7-diazaspiro[4.4]nona-3,8-diene-2,6-dione

Methyl 1-aryl-3-cinnamoyl-4,5-dioxo-4,5-dihydro-1H-pyrrole-2-carboxylates reacted with 4-benzylamino- and 4-arylaminopent-3-en-2-ones to give 1-aryl-7-benzyl- and 1,7-diaryl-9-acetyl-4-cinnamoyl-3-hydroxy-8-methyl-1,7-diazaspiro[4.4]nona-3,8-diene-2,6-diones. The crystalline and molecular structures of 9-acetyl-4-cinnamoyl-3-hydroxy-1-(4-methoxyphenyl)-8-methyl-7-phenyl-1,7-diazaspiro[4.4]nona-3,8-diene-2,6-dione were studied by X-ray analysis.     

Azolyl-substituted 1,2,3-triazoles

Huisgen reaction of (E)-1,5-diarylpent-2-en-4-yn-1-ones and (E)-1,5-diarylpent-1-en-4-yn-3-ones afforded 1-aryl-3-(5-aryl-1H-1,2,3-triazol-4-yl)prop-2-en-1-ones and 3-aryl-1-(5-aryl-1H-1,2,3-triazol-4-yl)-prop-2-en-1-ones, respectively. (E)-1-Aryl-3-(5-phenyl-1H-1,2,3-triazol-4-yl)prop-2-en-1-ones reacted with hydrazine hydrate and phenylhydrazine to give 72–93% of 4-(3-aryl-4,5-dihydro-1H-pyrazol-5-yl)-5-phenyl-1H-1,2,3-triazoles which underwent dehydrogenation on heating in boiling acetic acid with formation of the corresponding pyrazole derivatives. The molecular structures of (E)-3-phenyl-1-(5-phenyl-1H-1,2,3-triazol-4-yl)prop-2-en-1-one and 4-[3-(4-methylphenyl)-1-phenyl-4,5-dihydro-1H-pyrazol-5-yl]-5-phenyl-1H-1,2,3-triazole were studied by X-ray analysis. 4-(3-Aryl-4,5-dihydro-1H-pyrazol-5-yl)-5-phenyl-1H-1,2,3-triazoles showed toxicity against Daphnia magna.     

Regioselective synthesis of 4-alkyl- and 4-aryl-6-(perfluoroalkyl)salicylic acid derivatives by formal [3+3] cyclocondensation of 1,3-bis(silyloxy)-1,3-butadienes with 3-silyloxy-1-(perfluoroalkyl)prop-2-en-1-ones

4-Alkyl- and 4-aryl-6-(perfluoroalkyl)salicylic acid derivatives were regioselectively prepared by [3+3] cyclization of 1,3-bis(silyl enol ethers) with 3-silyloxy-1-(perfluoroalkyl)prop-2-en-1-ones.     

Direct heterocyclization of tetrahydroisoquinolin-1-ylideneacetic acids by the action of 5-arylfuran-2,3-diones

Aroylketenes generated in situ by thermolysis of 6-aryl-2,2-dimethyl-4H-1,3-dioxin-4-ones reacted with 3,3-dialkyl-1-methyl-3,4-dihydroisoquinolines to give (1Z,3Z)-4-aryl-4-hydroxy-1-[3,3-dialkyl-3,4-dihydroisoquinolin-1(2H)-ylidene]but-3-en-4-ones. The crystalline and molecular structure of (1Z,3Z)-4-hydroxy-1-[6,7-dimethoxy-3,3-dimethyl-3,4-dihydroisoquinolin-1(2H)-ylidene]-4-phenylbut-3-en-2-one was studied by X-ray diffraction.     

Synthesis of spiro- and dispirotetrahydropyrane-2,4-diones involving cyclobutane fragment in position 5 of heterocycle

Methyl 3-(1-bromocyclobutyl)-2,2-dimethyl-3-oxopropanoates, 1-(1-bromocyclobutyl-carbonyl) cyclopentanoates and 1-(1-bromocyclobutylcarbonyl)cyclobutanoates react with zinc and aromatic aldehydes to form 5-aryl-8,8-dimethyl-6-oxaspiro[3.5]nonane-7,9-diones, 13-aryl-12-oxadispiro[3.1.4.3]tridecane-5,11-diones and 12-aryl-11-oxadispiro[3.1.3.3]dodecane-5,10-diones respectively.     

新型环烷烯并嘧啶并噻唑-3-酮类化合物的合成

以环戊酮、环庚酮为起始原料合成的环烷烯并[1,2-d]嘧啶-2-硫酮(2)与氯乙酸、芳香醛反应, 合成具有潜在抗癌活性的稠合杂环化合物5-芳基-2,8-二芳亚甲基-2,3,6,7-四氢-5H,8H-环戊烯并[1,2-d]噻唑并[3,2-a]嘧啶-3-酮(3)以及5-芳基-2,10-二芳亚甲基-2,3,6,7,8,9-六氢-5H,10H-环庚烯并[1,2-d]噻唑并[3,2-a]嘧啶-3-酮(4). 3和4的结构经¹H NMR, IR, MS分析确认.