New Three-Component Reaction:  Novel Formation of a Seven-Membered Ring by the Unexpected Reaction at the γ-Position of the β-Keto Ester

2007 ◽  
Vol 9 (9) ◽  
pp. 1687-1690 ◽  
Author(s):  
Hiromichi Fujioka ◽  
Kenichi Murai ◽  
Ozora Kubo ◽  
Yusuke Ohba ◽  
Yasuyuki Kita
Keyword(s):  
Membered Ring ◽  
Keto Ester ◽  
Three Component Reaction ◽  
Unexpected Reaction

scholarly journals New Three-Component Reaction: Novel Formation of a Seven-Membered Ring by the Unexpected Reaction at the γ-Position of the β-Keto Ester.

ChemInform ◽  
2007 ◽  
Vol 38 (36) ◽  
Author(s):  
Hiromichi Fujioka ◽  
Kenichi Murai ◽  
Ozora Kubo ◽  
Yusuke Ohba ◽  
Yasuyuki Kita
Keyword(s):  
Membered Ring ◽  
Keto Ester ◽  
Three Component Reaction ◽  
Unexpected Reaction

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.

Highly Enantioselective Biginelli Reaction of Aliphatic Aldehydes Catalyzed by Chiral Phosphoric Acids

Synlett ◽  
2017 ◽  
Vol 28 (15) ◽  
pp. 2041-2045 ◽  
Author(s):  
Yongbiao Guo ◽  
Chuanpin Zou ◽  
Zhenhua Gao ◽  
Xiangyan Meng ◽  
Guilan Huang ◽  
...  
Keyword(s):  
Phosphoric Acid ◽  
Biginelli Reaction ◽  
Aliphatic Aldehyde ◽  
Reaction Conditions ◽  
Aliphatic Aldehydes ◽  
Keto Ester ◽  
Chiral Phosphoric Acid ◽  
Three Component Reaction ◽  
High Yields ◽  
Phosphoric Acids

Several chiral phosphoric acids were evaluated as organocatalysts for the enantioselective Biginelli reaction of aliphatic aldehydes. With a chiral phosphoric acid derived from 3,3′-bis(3,5-di-tert-butyl-4-methoxyphenyl)-1,1′-binaphthalene-2,2′-diol, and after extensive optimization of the reaction conditions, the corresponding dihydropyrimidines were obtained in moderate to high yields with 73–87% ee by a three-component reaction of an aliphatic aldehyde, urea, and a β-keto ester.

scholarly journals The Flögel-three-component reaction with dicarboxylic acids – an approach to bis(β-alkoxy-β-ketoenamides) for the synthesis of complex pyridine and pyrimidine derivatives

2014 ◽  
Vol 10 ◽  
pp. 394-404 ◽  
Author(s):  
Mrinal K Bera ◽  
Moisés Domínguez ◽  
Paul Hommes ◽  
Hans-Ulrich Reissig
Keyword(s):  
Dft Calculations ◽  
Carboxylic Acids ◽  
Aromatic Compounds ◽  
Dicarboxylic Acids ◽  
Membered Ring ◽  
Simple Synthesis ◽  
Pyrimidine Derivatives ◽  
Three Component Reaction ◽  
Palladium Catalyzed ◽  
Pyridine And Pyrimidine Derivatives

An extension of the substrate scope of the Flögel-three-component reaction of lithiated alkoxyallenes, nitriles and carboxylic acids is presented. The use of dicarboxylic acids allowed the preparation of symmetrical bis(β-ketoenamides) from simple starting materials in moderate yields. Cyclocondensations of these enamides to 4-hydroxypyridine derivatives or to functionalized pyrimidines efficiently provided symmetrically and unsymmetrically substituted fairly complex (hetero)aromatic compounds containing up to six conjugated aryl and hetaryl groups. In addition, subsequent functionalizations of the obtained heterocycles by palladium-catalyzed couplings or by oxidations are reported. We also describe the simple synthesis of a structurally interesting macrocyclic bispyrimidine derivative incorporating a 17-membered ring, whose configuration was elucidated by DFT calculations and by subsequent reactions.

An Unprecedented Synthesis of Eight-Membered-Ring Cyclic Thioimidic Esters by a Three-Component Reaction

Synthesis ◽  
2009 ◽  
Vol 2009 (16) ◽  
pp. 2733-2736 ◽  
Author(s):  
Abdolali Alizadeh ◽  
Reza Hosseinpour
Keyword(s):  
Membered Ring ◽  
Three Component Reaction

Straightforward Synthesis of Succinimide-Fused Pyrrolizidines by A Three-Component Reaction of α-Diketone, Amino Acid, and Maleimide

Synthesis ◽  
2020 ◽  
Author(s):  
Hua Zhao ◽  
Hongbin Zhai ◽  
Peng Shen ◽  
Yeting Guo ◽  
Jian Wei ◽  
...  
Keyword(s):  
Amino Acids ◽  
Amino Acid ◽  
Functional Group ◽  
High Efficiency ◽  
Cycloaddition Reaction ◽  
Azomethine Ylide ◽  
High Yield ◽  
One Pot ◽  
Keto Ester ◽  
Three Component Reaction

AbstractAn efficient, one-pot, three-component [3+2] cycloaddition reaction of azomethine ylide obtained from α-dicarbonyl compounds (cyclic and acyclic diketone or keto ester) and amino acids with maleimides under catalyst-free conditions has been developed. This cascade protocol shows high efficiency and remarkable functional group tolerance, and the ubiquitous succinimide-fused pyrrolizidines with a highly compact and strained scaffold were obtained with high yield and excellent diastereoselectivity. Furthermore, this novel and atom-economical strategy could be performed on a gram scale with comparable reaction efficiency.

scholarly journals Synthesis of 6-Membered-Ring Fused Thiazine-Dicarboxylates and Thiazole-Pyrimidines via One-Pot Three-Component Reactions

Molecules ◽  
2021 ◽  
Vol 26 (18) ◽  
pp. 5493
Author(s):  
Reagan L. Mohlala ◽  
Elena Mabel Coyanis ◽  
Muhammad Q. Fish ◽  
Manuel A. Fernandes ◽  
Moira L. Bode
Keyword(s):  
Membered Ring ◽  
One Pot ◽  
Dialkyl Acetylenedicarboxylate ◽  
Reaction Method ◽  
Dialkyl Acetylenedicarboxylates ◽  
Acidic Proton ◽  
Three Component Reaction ◽  
Two Component

A facile and efficient one-pot three-component reaction method for the synthesis of thiazine-dicarboxylates is reported. Reaction of an isocyanide and dialkyl acetylenedicarboxylate with 2-amino-4H-1,3-thiazin-4-one derivatives containing both an acidic proton and an internal nucleophile gave the products in good yields of 76–85%. The reactivity of dialkyl acetylenedicarboxylates was further tested in the synthesis of thiazole-pyrimidines where a two-component reaction of 2-aminothiazole with dialkyl acetylenedicarboxylates was successfully converted to a more efficient three-component reaction of a thiourea, α-haloketone and dialkyl acetylenedicarboxylate (DMAD/DEtAD) to give thiazole-pyrimidines in good yields of 70–91%.

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