10408-65-8

Upstream product

• 38060-48-9 2-phenyl-cyclopenta[a]naphthalene-1,3-dione 
• 10408-69-2 2,3-Diphenyl-3-(2'-naphthyl)-3-hydropropionsaeure 
• 501-65-5 diphenyl acetylene 
• 2243-83-6 2-naphthaloyl chloride 
• 103408-15-7 iodo-2 naphthalene carbonitrile-1 
• 66-77-3 1-naphthaldehyde 
• 2459-24-7 methyl 1-naphthoate 
• 86-55-5 1-naphthalenecarboxylic acid 
• 86-53-3 1-Cyanonaphthalene 
• 879-18-5 naphthalene-1-carbonic acid chloride 

Relevant academic research and scientific papers

Mechanochemical Solvent-Free Synthesis of Indenones from Aromatic Carboxylic Acids and Alkynes

The mechanochemical solvent-free synthesis of indenones from aromatic carboxylic acids and alkynes was achieved through triflic anhydride (Tf2O)-induced cyclization reaction. A variety of indenones including a bioactive PPARγagonist were obtained in up to 90% yield at room temperature. The present protocol has the advantages of mild reaction conditions, high reaction efficiency, and feasibility of scalable synthesis, providing a facile and sustainable route to diverse indenones.

Divergent Synthesis of α-Aroyloxy Ketones and Indenones: A Controlled Domino Radical Reaction for Di- A nd Trifunctionalization of Alkynes

Three different modes of aldehyde/alkyne assembly through a controlled radical reaction are devised. While a double C-H activation/annulation leads to indenones, a concurrent oxidation of both aldehydes and alkynes in the course of their connection offers

Cobalt(III)-catalyzed annulation of esters and alkynes: A facile route to indenones

An efficient protocol for the synthesis of indenones has been developed via the annulation of benzoic esters and internal alkynes by exploiting the cobalt catalyst.

Rhodium-catalyzed direct annulation of aldehydes with alkynes leading to indenones: Proceeding through in situ directing group formation and removal

The Rh-catalyzed direct annulation of an aldehyde with an alkyne leading to indenone was achieved. The in situ temporal installation of acetylhydrazine enables the annulation of the ortho arene C-H bond with alkynes to form ketone hydrazone. Subsequently, the in situ directing group removal takes place since ketone hydrazone is more susceptible toward hydrolysis than aldehyde hydrazone. Notably, this procedure tolerates a series of functional groups, such as methoxyl, acetylamino, fluoro, trifluoromethyl, methoxycarbonyl, chloro, and bromo groups.

Carbopalladation of nitriles: Synthesis of 2,3-diarylindenones and polycyclic aromatic ketones by the Pd-catalyzed annulation of alkynes and bicyclic alkenes by 2-iodoarenenitriles

2-Iodobenzonitrile, its derivatives, and various heterocyclic analogues undergo palladium(O)-catalyzed annulation onto diarylacetylenes or bicyclic alkenes to afford 2,3-diarylindenones and polycyclic aromatic ketones in very good to excellent yields. This reaction represents one of the first examples of the addition of an organopalladium moiety to the carbon-nitrogen triple bond of a nitrile. The reaction is compatible with a number of functional groups. A reaction mechanism, as well as a model accounting for the electronic effects of substituents on the aromatic ring of the nitrile, is proposed.

Thermal and Photochemical Reactions of η5-Cyclopentadienyl(naphthoyl)(dicarbonyl)iron Complexes with Alkynes: Formation of Benzindenones and Dihydropentalenones

η5-Cyclopentadienyl(1- and 2-naphthoyl)(dicarbonyl)iron complexes (6a) and (6b) have been synthesised from the appropriate acid chlorides and sodium η5-cyclopentadienyl(dicarbonyl)iron(1-).UV irradiation of (6a) and (6b) separately with diphenylacetylene in benzene gives 1,2-diphenyl-3H-benzinden-3-one (8), and 2,3-diphenyl-1H-benzinden-1-one (7) respectively, together with smaller quantities of bis(η5-cyclopentadienyl)(tetracarbonyl)di-iron.The benzindenones (7) and (8) are also formed in low yield from diphenylacetylene and η5-cyclopentadienyl(1- and 2-naphthoyl)(dicarbonyl)iron complexes respectively, in hot decalin.A second product from the thermal reaction is c-4,c-6a-dihydro-4-(1- or 2-naphthyl)-2,3-diphenylpentalen-1(r-3aH)-one (9a) or (9b), respectively, incorporating a cyclopentadienyl group.A compound of the last type (9c) is also formed in a thermal reaction of η5-cyclopentadienyl(1-naphthoyl)(dicarbonyl)iron with 1-phenylpropyne.The molecular structures of (7) and (9a) were elucidated by X-ray crystallography.