- Synthesis of 1,4-diketones by reaction of bicyclic lactams derived from 4-oxoalkanoic acids with organolithium compounds
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Bicyclic lactams obtained from ethyl 4-oxoalkanoates and 2-aminoethanol add saturated and unsaturated aliphatic lithium compounds forming the corresponding 1,4-diketones in 41-61% yield after acidic hydrolysis.
- Wedler,Schick
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- Synthesis of Diketones, Ketoesters, and Tetraketones by Electrochemical Oxidative Decarboxylation of Malonic Acid Derivatives: Application to the Synthesis of cis-Jasmone
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Disubstituted malonic acid derivatives are smoothly converted into diketones and ketoesters in good to excellent yield (68% to 91%) under electrochemical conditions. The scope can be extended to transform trisubstituted bis-malonic acids into tetraketones in 77% to 86% yield. The new method was applied to the total synthesis of cis-jasmone.
- Ma, Xiaofeng,Dewez, Damien F.,Du, Le,Luo, Xiya,Markó, István E.,Lam, Kevin
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- Synthesis of Diketones, Ketoesters, and Tetraketones by Electrochemical Oxidative Decarboxylation of Malonic Acid Derivatives: Application to the Synthesis of cis-Jasmone
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Disubstituted malonic acid derivatives are smoothly converted into diketones and ketoesters in good to excellent yield (68% to 91%) under electrochemical conditions. The scope can be extended to transform trisubstituted bis-malonic acids into tetraketones in 77% to 86% yield. The new method was applied to the total synthesis of cis-jasmone.
- Ma, Xiaofeng,Du, Le,Luo, Xiya,Markó, István E.,Dewez, Damien F.,Lam, Kevin
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p. 12044 - 12055
(2019/03/01)
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- Synthesis of cis-Jasmone
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cis-Jasmone 1, an important olfactive ingredient of jasmine flower oil, was synthesized by starting from methyl 3-formylpropionate 2 in a 24 percent overall yield in 7 steps.
- Tsukasa, Hidetaka
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p. 1181 - 1182
(2007/10/02)
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- Hydroacylation of Alkyl Vinyl Ketones and Acrylic Esters Using Organotetracarbonylferrates. Synthesis of 1,4-Dicarbonyl Compounds
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Alkyl vinyl ketones and acrylic esters were hydroacylated with organotetracarbonylferrates to the corresponding 1,4-diketones and 4-oxo carboxylic acid derivatives in good yield in dipolar aprotic solvents such as N,N-dimethylacetamide.Addition of 18-crown-6 improved the yield. cis-Jasmone and γ-jasmolactone were synthesized by use of these reactions.
- Yamashita, Masakazu,Tashika, Haruyoshi,Uchida, Masaya
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p. 1257 - 1261
(2007/10/02)
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- A facile synthesis of 1,4-diketones
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1,4-Diketones may conveniently be synthesized by the addition of 2-methylcyclopropenyllithium to N-methoxy-N-methylcarboxamides followed by hydrolysis of intermediate cyclopropyl ketone adducts on silica gel. The new method has been applied to the synthesis of cis-jasmone.
- Bergman,Nilsson,Wickberg
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p. 2783 - 2786
(2007/10/02)
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- Hydroacylation of Simple Alkyl Vinyl Ketones Using Organotetracarbonylferrates
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Alkyl vinyl ketones were hydroacylated by organotetracarbonylferrates to the corresponding 1,4-diketones in good yields in dipolar aprotic solvents such as dimethylacetamide.The addition of 18-Crown-6 made an increase of the yields.
- Yamashita, Masakazu,Tashika, Haruyoshi,Suemitsu, Rikisaku
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p. 691 - 692
(2007/10/02)
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- (Z)-7-NITRO-3-HEPTENE AS CENTRAL INTERMEDIATE FOR THE SYNTHESIS OF JASMONE, METHYL JASMONATE, AND γ-JASMONOLACTONE
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(Z)-7-Nitro-3-heptene is used as central intermediate in the synthesis of jasmone (13), methyl jasmonate (15), and γ-jasmonolactone (16), three jasmin constituents.Conjugate addition of the title compound, by heterogeneous catalysis, to methyl vinyl ketone, or acrolein, or methyl acrylate, followed by Nef reaction, affords (Z)-undec-8-ene-2,5-dione, (Z)-1,4-dioxo-dec-7-ene, and (Z)-4-oxo-dec-7-enoic acid methyl ester respectively, which are easily converted into jasmone, methyl jasmonate and γ-jasmonolactone.
- Ballini, Roberto,Petrini, Marino,Marotta, Emanuela
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p. 575 - 584
(2007/10/02)
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- A NEW READY ROUTE TO 1,4-KETOALDEHYDES AND 1,4-DIKETONES WITH APPLICATION TO THE SYNTHESIS OF Z-JASMONE AND DIHYDROJASMONE
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A new three-step synthesis in good overall yield of 1,4-ketoaldehydes and 1,4-diketones is described.The method involves two sequential coupling reaction of reagents with S-phenyl carbonochloridothioate in the presence of nickel(II) or iron(III) complexes as catalysts.Application of this reaction to the synthesis of Z-jasmone and dihydrojasmone is also described.
- Fiandanese, V.,Marchese, G.,Naso, F.
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p. 3587 - 3590
(2007/10/02)
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- Synthesis and Application of Imidazole Derivatives: Preparation of Various Diketones from 1,n-Bis(1-methyl-1H-imidazol-2-yl)alkane-1,n-diones
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Reaction of 1,n-bis(1-methyl-1H-imidazol-2-yl)alkane-1,n-dione (8) with an excess of Grignard reagent was examined.In the cases of n = 4 and 5, precursors (14) for synthesis of various asymmtric 1,4- and 1,5-diketones (12: R1 R2), respectively, were obtained in good yields by treating 8 with an excess of methylmagnesium iodide in ether followed by trimethylsilylation.In the case of n >/= 8, the two carbonyl groups of 8 were both attacked by the Grignard reagent, and the products (11: R1=R2=CH3) were convertible to symmetrical diketones (12: R1=R2=CH3) in good yields.In cases of n = 6 and 7, the mode of the Grignard reaction was transitional between the two types.Keywords - 2-acyl-1H-imidazole; 1,n-bis(1-methyl-1H-imidazol-2-yl)-1,n-alkanedione; diketone synthesis; asymmetric diketone; symmetric diketone; Grignard reaction; dihydrojasmone; cis-jasmone; muscone; 2-(1-hydroxy-1-alkyl)-1-methyl-1H-imidazole
- Hayakawa, Satoshi,Baba, Junko,Okamoto, Masao,Ohta, Shunsaku
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- MICHAEL ADDITION OF NOVEL ACYL ANION EQUIVALENTS GENERATED BY THE ELECTROREDUCTION OF OXAZOLINIUM SALTS TO ACTIVATED OLEFINS
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Electroreduction of oxazolinium salts gave novel acyl anion equivalents (AAEs), and the Michael addition of these AAEs to activated olefins has been found to be promoted effectively by the addition of chlorotrimethylsilane into the reaction system.This reaction was applied to the synthesis of cis-jasmone and dihydrojasmone.
- Shono, Tatsuya,Kashimura, Shigenori,Yamaguchi, Yoshihide,Kuwata, Fumitaka
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p. 4411 - 4414
(2007/10/02)
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- SYNTHESES OF DIKETONIC INTERMEDIATES FOR THE TOTAL SYNTHESES OF DIHYDROJASMONE, cis-JASMONE AND dl-MUSCONE STARTING FROM 1,n-DI(1-METHYL-1H-IMIDAZOL-2-YL)-1,n-ALKANEDIONE
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2,15-Dihydroxy-2,15-di(1-methyl-1H-imidazol-2-yl)hexadecane (3) was obtained by treating 1,14-(1-methyl-1H-imidazol-2-yl)-1,14-tetradecadione (2b) with an excess of CH3MgI, while 1,4-di(1-methyl-1H-imidazol-2-yl)-4-trimethylsilyloxy-2-pentanone (6; R1 = TMS) was obtained by the similar treatment of 1,4-(1-methyl-1H-imidazol-2-yl)-1,4-butadione (2a) followed by trimethylsilylation.These products (3 and 6) were convertible into the known diketonic intermediates for the synthesis of dl-muscone, dihydrojasmone and cis-jasmone.
- Ohta, Shunsaku,Hayakawa, Satoshi,Tamai, Yoshimi,Yuasa, Teruyuki,Okamoto, Masao
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p. 141 - 146
(2007/10/02)
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- A New, Short Synthesis of Z-Jasmone
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Z-Jasmone (1) was prepared from ethylene ketal of O,O-diethyl-4-oxo-pentanephosphonate (2) in four steps in 36percent overall yield.A key step in this synthesis is the oxygenation of the α-phosphonate carbanion generated from the monoalkylation product of 2 with Z-3-hexen-1-yl iodide (3). - Keywords: Z-Jasmone Synthesis, Ethylene Ketal, O,O-diethyl-4-oxo-pentanephosphonate, Z-3-Hexen-1-yl Iodide
- Mikolajczyk, Marian,Midura, Wanda
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p. 263 - 264
(2007/10/02)
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- NEW SYNTHETIC METHOD OF (Z)-4-ALKENOIC ACIDS USING RING-OPENING REACTION OF (Z)-4-HEXENOLIDE WITH ORGANOCOPPER REAGENT
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(Z)-4-Hexenolide reacted regioselectively with diorganocuprates to give (Z)-4-alkenoic acids in high yields.Synthetic utility was demonstrated by the convenient synthesis of cis-jasmone.
- Fujisawa, Tamotsu,Umezu, Kazuto,Kawashima, Masatoshi
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p. 1795 - 1798
(2007/10/02)
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- A Short Synthesis of Dihydrojasmone, cis- and trans-Jasmones
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The titled jasmones were synthesized from N,N'-dimethyl-2-oxo-1,3-propanedisulfoanilide, a new three carbon building block for organic preparation.
- Ogura, Fumio,Otsubo, Tetsuo,Sakamoto, Tetsuo,Yamaguchi, Hachiro
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p. 1691 - 1692
(2007/10/02)
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- A NEW ROUTE TO 1,4-DIKETONES AND ITS APPLICATION TO (Z)-JASMONE AND DIHYDROJASMONE SYNTHESIS.
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(Z)-Jasmone, dihydrojasmone and other 3-methylcyclopent-2-en-1-ones are easily synthetized starting from aldehydes and 1-(2-methyl-1,3-dioxolane-2-yl)-2-nitroethane as reagent for 3-ketobutyl anion synthon.Nitro-aldol condensation is the chainleghtening reaction followed by oxidation and denitration via p-toluenesulfonylhydrazones of the corresponding α-nitroketones.Removal of protecting groups gives 1,4-diketones which are then cyclized with alkali.
- Rosini, Goffredo,Ballini, Roberto,Sorrenti, Pietro
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p. 4127 - 4132
(2007/10/02)
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- A Convenient Preparative Method of Jasmone and its Related Compounds
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The reaction of (Z)-hept-4-enoic acid (1) with vinylmagnesium bromide gave (Z)-undeca-1,8-dien-5-one (2).The oxidation of the terminal vinylic group of (2) affords (Z)-undec-8-ene-2,5-dione (3).Jasmone (4) was obtained by the usual alkali cyclization of (3).A variety of alkylcyclopentenones were prepared by the same method.
- Watanabe, Shoji,Fujita, Tsutomu,Suga, Kyoichi,Haibara, Michio
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p. 1739 - 1741
(2007/10/02)
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- Jasmonoid Synthesis from cis-4-Heptenoic Acid
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Jesmonoids with cis-2-pentenyl side-chain such as cis-jasmone, methyl jasmonate, and jasmolone were easily synthesized from cis-4-heptenoic acid obtained by the ring opening reaction of β-propiolactone with di-cis-butenylcuprate.
- Sato, Toshio,Kawara, Tatsuo,Sakata, Kazumi,Fujisawa, Tamotsu
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p. 505 - 508
(2007/10/02)
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- SYNTHESE DE MONODIOXOLANNES DE DICETONES-1,4 ET DE DICETONES-1,4 AU MOYEN DES ANHYDRIDES MIXTES CARBOXYLIQUES ET CARBONIQUES: APPLICATION A LA PREPARATION DE LA DIHYDROJASMONE, DE LA Z-JASMONE ET DE LA DEHYDROJASMONE
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Levulinic acid 1 is easily converted by two steps into mixed carboxylic and carbonic anhydride 3 which reacts with the organolithium reagent issued from trimethylsilyl esters.Monoethylene acetal of 1,4-diketones 4 can be prepared; it is also possible to obtain 1,4-diketones 5 in one step by hot acid hydrolysis.The preparation of the dihydrojasmone 6d, Z-jasmone 6e and dehydrojasmone 6f shows the efficiency of the process.
- Moreau, J.-L.,Couffignal, R.,Arous-Chtara, R.
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p. 307 - 310
(2007/10/02)
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- New Routes to cis-Jasmone and Dihydrojasmone via 1,4-Diketones Exploiting the Mobile Activating Sulfonyl Group
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cis-Jasmone(1a) and dihydrojasmone(1b) are synthesized starting from cis-3-hexen-1-yl phenyl sulfone (6a) and n-hexyl phenyl sulfone (6b), respectively, through 1,4-diketones 3a,b.The key intermediates in these syntheses are the diketo sulfones 7a,b, which are prepared by two methods.The reaction of dilithiosulfones 12a,b with γ-valerolactone in tetrahydrofuran in the presence of hexamethylphosphoramide at -78 deg C gives the hydroxy keto sulfones 13a,b in satisfactory yields and the successive oxidation of these compounds with Jones reagent in acetone affords 7a,b in very good yields.On the other hand, the reaction of 12a,b with ethyl levulinate ethylene ketal gives the partially protected diketo sulfones 17a,b, from which 7a,b are obtained by removal of the protecting group.Cleavage of the carbon-sulfur bond in 7a,b, accomplished by aluminum amalgam in aqueous tetrahydrofuran, affords 3a,b which are then cyclized to 1a,b by heating over basic alumina in benzene.
- Mussatto, Maria Cristina,Savoia, Diego,Trombini, Claudio,Umani-Ronchi, Achille
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p. 4002 - 4005
(2007/10/02)
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