1357394-80-9

Upstream product

• 6630-33-7 ortho-bromobenzaldehyde 
• 768-60-5 4-methoxyphenylacetylen 
• 33675-41-1 1-bromo-2-(4-methoxyphenyl)acetylene 

Downstream Products

• 1203669-21-9 1-(2-bromophenyl)-3-(4-methoxyphenyl)prop-2-yn-1-one 
• 3813-92-1 2-(4-methoxyphenyl)-1,4-dihydro-4-oxoquinoline 
• 1415988-80-5 3-(2-bromophenyl)-5-(4-methoxyphenyl)-1-phenyl-4,5-dihydropyrazole 

Relevant academic research and scientific papers

Nitromethane as a Carbanion Source for Domino Benzoannulation with Ynones: One-Pot Synthesis of Polyfunctional Naphthalenes and a Total Synthesis of Macarpine

A one-pot, transition-metal-free, domino Michael/SNAr protocol of general applicability has been devised for the regioselective synthesis of polyfunctional naphthalenes by employing nitromethane and ortho-haloaryl ynones. Utilization of nitromethane as a one carbon carbanion source that is incorporated into a variety of ynones, ends up as an aromatic nitro substituent. The application of this domino process towards a total synthesis of the polycyclic alkaloid macarpine demonstrate for the efficacy of this methodology. The conceptually simple approach to affect regioselective, multifunctional benzoannulation of ynones displays wide substrate scope and functional-group tolerance and has been implemented with substituted nitromethanes, as well as with alicyclic o-haloynones.

Selective Insertion of Alkynes into C-C σ Bonds of Indolin-2-ones: Transition-Metal-Free Ring Expansion Reactions to Seven-Membered-Ring Benzolactams or Chromone Derivatives

An unprecedented ring expansion reaction of indolin-2-ones with alkynyl ketones under transition-metal-free conditions has been developed. Base-promoted selective cleavage of a C-C σ bond of the amide is the key in this process, which provides a straightf

Access to 2-Alkyl/Aryl-4-(1 H)-Quinolones via Orthogonal "nH3" Insertion into o-Haloaryl Ynones: Total Synthesis of Bioactive Pseudanes, Graveoline, Graveolinine, and Waltherione F

An efficient one-pot synthesis of 4-(1H)-quinolones through an orthogonal engagement of diverse o-haloaryl ynones with ammonia in the presence of Cu(I), involving tandem Michael addition and ArCsp2-N coupling, is presented. The substrate scope of this convenient protocol, wherein ammonium carbonate acts as both an in situ ammonia source and a base toward diverse 2-substituted 4-(1H)-quinolones, has been mapped and its efficacy validated through concise total synthesis of bioactive natural products pseudanes (IV, VII, VIII, and XII), graveoline, graveolinine, and waltherione F.

Base-mediated insertion reaction of alkynes into carbon-carbon σ-bonds of ethanones: synthesis of hydroxydienone and chromone derivatives

Transition-metal free insertions of alkynes into carbon-carbon σ-bonds of ethanones have been reported. These tandem reactions offer an efficient synthesis of hydroxydienones and multi-substituted chromones. This is the first example of base-promoted insertion reactions of isolated carbon-carbon triple bonds into carbon-carbon σ-bonds with active methylene compounds bearing only one electron-withdrawing group.

Base-Promoted Tandem Reaction towards Conjugated Dienone or Chromone Derivatives with a Cyano Group: Insertion of Alkynes into C–C σ-Bonds of 3-Oxopropanenitriles

Base-promoted insertion reactions of alkynes into the C–C σ-bonds of α-cyano ketones were established to construct highly functionalized conjugated olefins or chromone derivatives via transition metal-free tandem reactions. These reactions are initialized through the nucleophilic attack of α-cyano ketones to alkynones followed by intramolecular nucleophilic addition/ring-opening to furnish the cyano-containing alkenes. In the cases of alkynones bearing an ortho-halide-substituted aryl ring, a further C–O bond coupling reaction occurs to afford chromone derivatives in good to high yields. Various alkynones bearing alkyl or aryl substituents were compatible in the reaction. This reaction has the potential to become a general synthetic protocol for the preparation of cyano-substituted olefins and chromones due to the abundance of easily accessible starting materials possessing diverse substituent groups. (Figure presented.).

Stitching Oxindoles and Ynones in a Domino Process: Access to Spirooxindoles and Application to a Short Synthesis of Spindomycin B

A general, transition-metal-free, one-pot, domino Michael-SNAr or AdNE substitution protocol was devised for spiroannulation of oxindoles with ortho-bromoaryl ynones, β-bromoalkenyl ynones, and β-bromoalkenyl enones in a convenient a

Insertion of Isolated Alkynes into Carbon–Carbon σ-Bonds of Unstrained Cyclic β-Ketoesters via Transition-Metal-Free Tandem Reactions: Synthesis of Medium-Sized Ring Compounds

The transition-metal-free insertion of isolated alkynes into carbon–carbon σ-bonds of unstrained cyclic β-dicarbonyl compounds has been reported. These tandem reactions offer an efficient synthesis of medium-sized ring or fused-ring compounds through ring expansion. The methodology has the potential to be widely used throughout organic synthesis due to the easily accessible starting materials and mild reaction conditions.

A mild, highly efficient addition of alkynes to aldehydes catalyzed by titanium dioxide-supported silver nanoparticles

Titanium dioxide-supported silver nanoparticles were utilized as a highly efficient catalyst for the addition of terminal alkynes to aldehydes to prepare propargylic alcohols with the promotion by triphenylphosphine. Both a significant support effect and a ligand effect were observed in the catalytic reaction. With this protocol, various propargylic alcohol derivatives were synthesized from aldehydes and terminal alkynes in good to excellent yields. Furthermore, the catalyst could be recovered and reused effectively without obvious reduction in catalytic activity.

Palladium-catalyzed tandem amination reaction for the synthesis of 4-quinolones

(Figure presented) An efficient palladium-catalyzed tandem amlnatlon approach was developed In one step to afford functlonallzed 4-qulnolones In good to excellent ylelds from easlly accessible o-haloaryl acetylenlc ketones and primary amines.