Facile Synthesis of β-Keto Esters from Methyl Acetoacetate and Acid Chloride:  The Barium Oxide/Methanol System1

1998 ◽  
Vol 2 (6) ◽  
pp. 412-414 ◽  
Author(s):  
Yoshifumi Yuasa ◽  
Haruki Tsuruta ◽  
Yoko Yuasa
Keyword(s):  
Acid Chloride ◽  
Barium Oxide ◽  
Facile Synthesis ◽  
Methyl Acetoacetate ◽  
Keto Esters

Ring formation via β-keto ester dianions

1977 ◽  
Vol 55 (6) ◽  
pp. 996-1000 ◽  
Author(s):  
Phaik-Eng Sum ◽  
Larry Weiler
Keyword(s):  
Membered Ring ◽  
Ring Formation ◽  
Methyl Acetoacetate ◽  
Keto Ester ◽  
Keto Esters

The reaction of α,ω-dihalides with the dianion of methyl acetoacetate gives a mixture of mono- and bisalkylated products. The monoalkylated products can be cyclized via the monoanion to cyclic β-keto esters with a seven- or eight-membered ring. Alternatively these monoalkylated products can be cyclized via the dianion to γ-cyclopentyl- or γ-cyclohexyl-β-keto esters.

Synthesis of β- and β,β-substituted Morita–Baylis–Hillman adducts using a two-step protocol

2012 ◽  
Vol 90 (5) ◽  
pp. 450-463 ◽  
Author(s):  
David I. Magee ◽  
Same Ratshonka ◽  
Jessica McConaghy ◽  
Maggie Hood
Keyword(s):  
Knoevenagel Condensation ◽  
Condensation Reaction ◽  
Facile Synthesis ◽  
Aliphatic Aldehydes ◽  
Tert Butyl ◽  
Keto Esters ◽  
Knoevenagel Condensation Reaction

The synthesis of a large number of β- and β,β-substituted keto esters was successful by the use of the Knoevenagel condensation reaction. The stereoselectivity of these reactions was improved by alteration of various substituent groups. Although there were few examples of complete Z selectivity, the use of tert-butyl acetoacetate with either aromatic or aliphatic aldehydes afforded Z selectivity. The selective reductions of these substituted keto esters was successfully achieved by using a combination of NaBH4 and CeCl3·7H2O or Yb(OTf)3, which allowed a facile synthesis of a large number of stereochemically pure substituted Morita–Baylis–Hillman adducts, including β,β-substituted adducts.

Facile Synthesis of Aryl α-Keto Esters via the Reaction of Aryl Diazoacetate with H2O and DEAD.

ChemInform ◽  
2007 ◽  
Vol 38 (3) ◽  
Author(s):  
Zhenqiu Guo ◽  
Haoxi Huang ◽  
Qingquan Fu ◽  
Wenhao Hu
Keyword(s):  
Facile Synthesis ◽  
Keto Esters

Facile Synthesis of α-Keto Esters via A Free Radical Acylation Approach

Synlett ◽  
1997 ◽  
Vol 1997 (Sup. I) ◽  
pp. 475-476 ◽  
Author(s):  
Sunggak Kim ◽  
Joo-Yong Yoon ◽  
Ill Lee
Keyword(s):  
Free Radical ◽  
Facile Synthesis ◽  
Keto Esters

ChemInform Abstract: Direct, Facile Synthesis of N-Acyl-α-amino Amides from α-Keto Esters and Ammonia.

ChemInform ◽  
2009 ◽  
Vol 40 (4) ◽  
Author(s):  
Rukundo Ntaganda ◽  
Tamara Milovic ◽  
Jorge Tiburcio ◽  
Avinash N. Thadani
Keyword(s):  
Facile Synthesis ◽  
Keto Esters ◽  
Amino Amides

Structure of Reaction Products of Some Substituted Quinoxaline N-Oxides with Carbanions

1994 ◽  
Vol 59 (11) ◽  
pp. 2493-2500 ◽  
Author(s):  
Jaromír Toman ◽  
Jaromír Mindl ◽  
Antonín Lyčka ◽  
Jiří Klicnar ◽  
Ivana Srovnalová ◽  
...  
Keyword(s):  
Ring Closure ◽  
Reaction Products ◽  
Methyl Acetoacetate ◽  
Aziridine Ring ◽  
Keto Esters ◽  
Ethyl Methyl ◽  
The Difference

1,2,3-Triazolo[1,5-a]- (II) and 1,2,4-triazolo[4,3-a]quinoxaline 5-oxide (III) react with the carbanions of β-diketones and β-keto esters to give enaminones in the same way as their tetrazolo analogue. The difference in mechanism of reactions of these N-oxides with carbanions of 3-alkylpentane-2,4-dione and ethyl methyl acetoacetate giving aziridinopolyazoloquinoxalines and ethyl 2-(polyazoloquinoxalin-4-yl)propanoates, respectively, is discussed. It was shown that the reaction with carbanion including the aziridine ring closure proceeds with 3,4-dihydro-3-oxoquinoxaline-1-oxide as well.

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