60390-89-8

Upstream product

• 62-53-3 aniline 
• 2028-63-9 but-3-yn-2-ol 
• 41125-09-1 3-oxo-butyraldehyde; sodium enolate 
• 4652-27-1 4-methoxy-3-buten-2-one 
• 51731-17-0 trans-4-methoxy-3-buten-2-one 
• 187606-81-1 (3E)-4-(phenylamino)but-3-en-2-one 
• 1423-60-5 methyl ethynyl ketone 
• 4643-20-3 (E)-4-chloro-3-buten-2-one 
• 31172-37-9 trans-4-methoxybut-3-en-2-one 

Relevant academic research and scientific papers

A Method for the Preparation of β-Amino-α,β-unsaturated Carbonyl Compounds: Study of Solvent Effect and Mechanism

An efficient method for the preparation of β-amino-α,β-unsaturated carbonyl compounds is demonstrated. Bench-stable sodium 3-oxo-enolates were prepared from carbonyl compounds, and reacted with amines in the presence of an acid and a desiccant. DFT studie

Access to Highly Enantioenriched Donepezil-like 1,4-Dihydropyridines as Promising Anti-Alzheimer Prodrug Candidates via Enantioselective Tsuji Allylation and Organocatalytic Aza-Ene-Type Domino Reactions

This work aims at exploiting both the enantioselective Tsuji allylation of allyl carbonate 6 and an organocatalytic aza-ene-type domino reaction between enal 3a and β-enaminone 4a to develop a straightforward access to all of the four possible stereoisomers of a donepezil-like 1,4-dihydropyridine 1a (er up to 99.5:0.5; overall yield up 64%), an anti-Alzheimer's prodrug candidate. This strategy was extended to the preparation of other enantioenriched 1,4-dihydropyridines 1b-i (eight examples), highlighting its potential in the development of these chiral AChE inhibitors.

On water reaction of deactivated anilines with 4-methoxy-3-buten-2-one, an effective butynone surrogate

Poorly nucleophilic aromatic amines (nitroanilines, chloroanilines, etc.) react readily and selectively with trans-4-methoxy-3-buten-2-one, a convenient, effective and inexpensive surrogate for 3-butyn-2-one, to afford (Z)-enaminones. The efficiency of the reaction mostly lies in the use of water as a solvent, which enhances the reaction rate by a 45 to 200-fold factor with regard to other media.

Conjugate Addition of 3-Buytn-2-one to Anilines in Ethanol: Alkene Geometric Insights through in Situ FTIR Monitoring

A convenient, mild and effective conjugate addition of 3-butyn-2-one to a variety of anilines in ethanol is reported. The reaction was monitored and characterized through in situ FTIR, and the dynamics of the facile E/Z alkene geometry interconversion of the resultant aniline-derived enaminones was explored through NMR, FTIR and X-ray crystallography. A straightforward purification protocol that employs direct Kugelrohr distillation was identified, and the method was further extended to other amines and ynones, allowing rapid access to these interesting compounds.

Ruthenium complexes of electronically coupled cyclopentadienone ligands - Catalysts for transformations of propargyl alcohols

A series of donor- and acceptor-substituted ruthenium cyclopentadienone complexes were synthesized and their catalytic activities towards propargyl alcohols focused on amination reactions have been investigated. It is shown that the substituents of the cyclopentadienone ligand determine the mode of activation of propargyl alcohols by these complexes leading to different central intermediates in catalytic cycles. Catalytic transformations of propargyl alcohols to α- or β-amino ketones, enamino ketones, α,β-unsaturated imines, ketones, alkenes and conjugated enynes could be achieved. Wiley-VCH Verlag GmbH & Co. KGaA, 2007.

Ruthenium-catalyzed enaminoketone formation from propargyl alcohols

Monomeric ruthenium(0) complexes containing electronically coupled dienone ligands were found to catalyze the formation of enaminoketones from propargyl alcohols. Georg Thieme Verlag Stuttgart.

REACTION OF 1-ETHOXY-1-BUTEN-3-ONE WITH AMINES

In the reaction of 1-ethoxy-1-buten-3-one with ammonia and primary and secondary amines the alkoxy group is substituted by an amino group.In the reaction with ammonia 1-amino-1-buten-3-one condenses with the formation of 2-methyl-5-acetylpyridine.