Three-component reaction between substituted β-nitrostyrenes, β-dicarbonyl compounds and amines: diversity-oriented synthesis of novel β-enaminones

Abstract

The diversity-oriented synthesis of β-enaminones via three-component reaction between substituted β-nitrostyrenes, β-dicarbonyl compounds and amines is developed.

Resonance‐Assisted Hydrogen Bonding as a Driving Force in Synthesis and a Synthon in the Design of Materials

“…[95][96][97][98] Scheme5.Examples of RAHB-containing liquidc rystals (a,b) [103,104] and molecular receptors (c,d). [95][96][97][98] Scheme5.Examples of RAHB-containing liquidc rystals (a,b) [103,104] and molecular receptors (c,d).…”

“…Among his honors,h ew as awarded the Madinabeitia-LourenÅo Prize from the Spanish RoyalC hemical Society and the Prizes of the Portuguese Chemical and Electrochemical Societies. [29,43,82,83] These RAHB moieties are ubiquitous in variousf ields, includingo rganic [84][85][86] and inorganic synthesis, [87,88] crystal growth and design, [89][90][91][92] supramolecular chemistry, [93,94] medicinal chemistry, [95][96][97][98] and materials chemistry, [99,100] andh ave been used in the activation of covalent bonds, crystal engineering, dynamic combinatorial chemistry,m olecular recognition, E/Z isomeric resolution, racemization/epimerization of amino acids, solvatochromism, and liquid-crystalline materials, among other applications. [6] According to the electrostatic-covalent hydrogen bond model, the strongest H-bonds must be homonuclear( X ÀH···X) and symmetrical at both sides of the H-bond.O nly in this situation, the two wavefunctions corresponding to XÀH···X and X···HÀXr esonance forms are isoenergetic and can mix to agreater extent.…”

“…[6] According to the electrostatic-covalent hydrogen bond model, the strongest H-bonds must be homonuclear( X ÀH···X) and symmetrical at both sides of the H-bond.O nly in this situation, the two wavefunctions corresponding to XÀH···X and X···HÀXr esonance forms are isoenergetic and can mix to agreater extent. For instance, those moietiesa re found in many biologically active substances, such as GSK1265744, [95] harzianic acid, [96] (AE)-streptonigrin, [97] and herbicides [98] (Scheme 4), which are usually synthesized by using several synthetic procedures. The most typical cases of CAHB are strong hydrogenb onds formed between carboxylic acids and carboxylates, inorganic oxoacids and their conjugated bases, and very short intramolecular H-bonds in hydrogen maleate.…”

“…[95][96][97][98] Scheme5.Examples of RAHB-containing liquidc rystals (a,b) [103,104] and molecular receptors (c,d). This Review highlights the involvement of RAHB as ad riving force in the synthesis of organic,c oordination,a nd organometallic compounds,a sahandy tool in the activation of covalentb onds, and in startingm oieties for synthetic transformations.…”

Fabrication of Nano‐CuO@ZnO for the Synthesis of Functionalized β‐Enaminone Derivatives from β‐Nitrostyrenes, Aliphatic/Aromatic Amines and 1,3‐Dicarbonyl/4‐Hydroxy Coumarin

“…Recently, Wang et al . have reported a new method for the fabrication of β ‐enaminones via one‐pot multicomponent reaction of substituted β ‐nitrostyrenes, 1,3‐dicarbonyl compounds/4‐hydroxycoumarin and aliphatic amines.…”