17448-84-9

Upstream product

• 98-01-1 furfural 
• 141-97-9 ethyl acetoacetate 

Downstream Products

• 1298032-96-8 ethyl 5-cyano-6-[cyano(4'-phenyl-1',3'-selenazol-2'-yl)methyl]-4-(furan-2'-yl)-2-methyl-1,4-dihydropyridine-3-carboxylate 
• 1314236-52-6 (1S,2R,3R)-ethyl 2-formyl-3-(furan-2-yl)-5-hydroxy-1,2,3,6-tetrahydro-[1,1'-biphenyl]-4-carboxylate 
• 280573-96-8 5-amino-7-benzylselanyl-8-cyano-4-furan-2-yl-2-methyl-1,4-dihydro-[1,6]naphthyridine-3-carboxylic acid ethyl ester 
• 328236-95-9 5-amino-7-benzylseleno-8-cyano-3-ethoxycarbonyl-2-methyl-1,6-naphthyridine 
• 1352788-25-0 3-(α-furyl)-5-(2-hydroxyethyl)amino-2-ethoxycarbonyl-4-acetyl-1-methyl-4-cyclohexene-1-ol 
• 1352788-17-0 3-(α-furyl)-5-(3-hydroxypropyl)amino-2,4-diethoxycarbonyl-1-methyl-4-cyclohexen-1-ol 
• 1352788-16-9 3-(α-furyl)-5-(2-hydroxyethyl)amino-2,4-diethoxycarbonyl-1-methyl-4-cyclohexen-1-ol 

Relevant academic research and scientific papers

Asymmetric Synthesis of Pentasubstituted Cyclohexanes through Diphenylprolinol Silyl Ether Mediated Domino Michael/Michael Reaction

An asymmetric domino Michael/Michael reaction of α,β-unsaturated aldehydes 1 and α-acetyl-β-substituted-α,β-unsaturated esters 2 catalyzed by diphenylprolinol silyl ether was developed. This is a formal carbo [4+2] cycloaddition reaction affording penta-s

Cross-linked polystyrene-TiCl4 complex as a reusable Lewis acid catalyst for solvent-free Knoevenagel condensations of 1,3-dicarbonyl compounds with aldehydes

Cross-linked polystyrene copolymer beads with the average particle size in the range of (50–80 mesh size) were prepared by a new method, characterized and functionalized with titanium tetrachloride to afford the corresponding polystyrene?titanium tetrachloride complex in one step reaction and characterized by FT-IR, UV, TGA, DSC, XRD, SEM, BET. This polymer metal complex (PS/TiCl4) was used as a heterogeneous, recoverable, reusable Lewis acid for solvent-free Knoevenagel condensations of 1,3-diketones with aromatic aldehydes under green and mild conditions. The rate of reactions was found to decrease with an increasing percentage of crosslinking and the mesh size of the copolymer beads. This complex showed good stability and catalytic activity in the Knoevenagel reactions.

Enzyme catalytic promiscuity: The papain-catalyzed Knoevenagel reaction

Papain as a sustainable and inexpensive biocatalyst was used for the first time to catalyze the Knoevenagel reactions in DMSO/water. A wide range of aromatic, hetero-aromatic and α,β-unsaturated aldehydes could react with less active methylene compounds acetylacetone and ethyl acetoacetate. The products were obtained in moderate to excellent yields with Z/E selectivities of up to 100:0. This case of biocatalytic promiscuity not only widens the application of papain to new chemical transformations, but also could be developed into a potentially valuable method for organic synthesis.

Biocatalytic Knoevenagel reaction using alkaline protease from Bacillus licheniformis

BLAP (alkaline protease from Bacillus licheniformis) was used as a biocatalyst in the Knoevenagel condensations of aromatic, hetero-aromatic and α;β-unsaturated aldehydes with less reactive acetylacetone or ethyl acetoacetate. The reactions were performed in organic solvent in the presence of water. The functionalized trisubstituted alkenes and α,β,γ, δ-unsaturated carbonyl compounds could be obtained in moderate to good yields with E/Z selectivities up to >99:1. This biocatalytic reaction provided an alternative pathway for Knoevenagel condensation, which also demonstrates a novel case of unnatural activity of existing enzymes.

A facile synthesis of trisubstituted alkenes from β-diketones and aldehydes with AlCl3 as catalyst

Preparation of trisubstituted alkenes from low-activity β-diketones and aldehydes with aluminum chloride as catalyst has been studied. The frequently used catalyst AlCl3 is used for the first time to promote this condensation. The procedure is a convenient, low toxicity, and highly efficient method for industrial synthesis of trisubstituted alkenes in high yield. Springer Science+Business Media B.V. 2011.

Efficient solvent-free knoevenagel condensation between -diketone and aldehyde catalyzed by silica sulfuric acid

Silica sulfuric acid has been utilized as an efficient heterogeneous recyclable catalyst for Knoevenagel condensation between poorly reactive β-diketones and aldehydes under solvent-free conditions. This protocol also works well with more reactive β-ketoesters. The condensation is efficient, clean, and mild. The scope and generality of the Knoevenagel condensation were investigated. The procedure led only to the Knoevenagel product, and no side product derived from a subsequent Michael βaddition of -diketone to alkene was detected at rt. Increasing temperature led to a subsequent Michael addition, and it was applied to the efficient synthesis of 9-aryl-1,8-dioxo- octahydroxanthene derivatives.

A simple method for the preparation of functionalized trisubstituted alkenes and α,β,γ,δ-unsaturated carbonyl compounds by using natural amino acid l-tryptophan

Primary natural amino acid l-tryptophan was used, for the first time, as a catalyst in Knoevenagel condensations of aliphatic, aromatic, hetero-aromatic and α,β-unsaturated aldehydes with less reactive acetylacetone and ethyl acetoacetate. The reactions were carried out at room temperature and gave good yields. It is a convenient entry for preparation of functionalized trisubstituted alkenes and α,β,γ,δ-unsaturated carbonyl compounds.

Rearrangement of propargylic esters: Metal-based stereospecific synthesis of (E)- and (Z)-knoevenagel derivatives

Alkoxy-substituted propargylic esters undergo regioselective 1,3-acyloxy migration in the presence of Pt(II) and Cu(I) catalysts, allowing the preparation of α-ylidene-β-keto and -malonate esters. The reaction proved to also be stereodivergent as the Pt(II) and the Cu(I) catalysts perform the isomerization with complementary Z/E selectivity. Moreover, alkynyl-conjugated Knoevenagel products are produced from (bisalkynyl)methyl acetates. In such a case, the reaction is chemoselective as the 1,3-acetyl migration takes place through the alkoxyalkyne group in preference over the phenylalkyne group. The resulting (E)-alkynylenone unit suffers metal-catalyzed cyclization into the furyl ring, generating a copper(I) carbene species. Copyright

Neat reaction technology: A green tool

A solvent free approach for organic synthesis is described which involve microwave exposure of neat reactants. A variety of cyclization and condensation are carried out including the efficient one pot assembly of heterocyclic molecules from in situ genera

Neat reaction technology for the synthesis of novel 1,5-benzodiazepines

A convenient, solvent-free, green approach is described for the synthesis of novel 1,5-benzodiazepines by the reaction of ethylacetoacetate, aldehyde, and o-phenylenediamine without any catalyst at pH 7. Copyright Taylor & Francis Group, LLC.