109034-29-9

Upstream product

• 536-74-3 phenylacetylene 
• 1504-58-1 3-Phenyl-2-propyn-1-ol 
• 591-50-4 iodobenzene 
• 2579-22-8 Phenylpropargyl aldehyde 
• 768-60-5 4-methoxyphenylacetylen 
• 100-66-3 methoxybenzene 
• 7515-17-5 methyl 3-(4-methoxyphenyl)propynoate 

Downstream Products

• 14116-43-9 2-(4-methoxyphenyl)-6-phenyl-4H-pyran-4-one 
• 1443678-84-9 4-iodo-2-phenyl-5-(4-methoxy)phenylfuran-3-carbaldehyde 
• 1644599-49-4 4-iodo-2-(4-methoxyphenyl)-5-phenylfuran-3-carbaldehyde 
• 109034-41-5 2-(4-methoxyphenyl)-6-phenyltellura-4H-pyran-4-one 
• 109034-34-6 1-(4-methoxyphenyl)-5-phenyl-1,4-pentadiyn-3-one 

Relevant academic research and scientific papers

Regiodivergent Hydration-Cyclization of Diynones under Gold Catalysis

Skipped diynones, efficiently prepared from biomass-derived ethyl lactate, undergo a tandem hydration-oxacyclization reaction under gold(I) catalysis. Reaction conditions have been developed for a switchable process that allows selective access to 4-pyrones or 3(2H)-furanones from the same starting diynones. Further application of this methodology in the total synthesis of polyporapyranone B was demonstrated.

Transition Metal-Free Synthesis of 3-Alkynylpyrrole-2-carboxylates via Michael Addition/Intramolecular Cyclodehydration

A transition metal-free and efficient method for the synthesis of 3-alkynylpyrrole-2-carboxylates from diynones and glycine esters or 2-aminoacetophenone hydrochloride has been developed. This transformation provides a large range of substituted pyrroles in good to excellent yields with the elimination of water as the only by-product. The detailed mechanistic studies elucidated that this transformation involves a Michael addition/intramolecular cyclodehydration process. (Figure presented.) .

Synthesis of highly substituted 3-formylfurans by a gold(I)-catalyzed oxidation/1,2-alkynyl migration/cyclization cascade

3-Formylfuran derivatives are core structures of a variety of bioactive natural products. However, procedures for their preparation are still rare and generally inefficient in terms of atom economy: These methods require multiple steps or harsh reaction c

Bronsted acid catalyzed and NIS-promoted cyclization of diynones: Selective synthesis of 4-pyrone, 4-pyridone, and 3-pyrrolone derivatives

Bronsted acid catalyzed tandem cyclization was found to be highly effective for the preparation of a series of polysubstituted 4-pyrones from diynones (yield up to 99%). 4-Pyridone and 3-pyrrolone derivatives were also selectively synthesized by employing NIS and/or Bronsted acid. NIS as an electrophilic reagent could promote these reactions efficiently and rapidly under very mild reaction conditions.

Preparation of Arylpropiolate Esters from Trichlorocyclopropenium Cation and Elaboration of the Esters to Unsymmetrical 1,4-Pentadiyn-3-ones and Unsymmetrical Tellurapyranones

The addition of aromatic compounds including thiophene, naphthalene derivatives, and some benzene derivatives to trichlorocyclopropenium cation gave nearly quantitative yields of 1-aryl-2,3,3-trichlorocyclopropenes.Alcoholysis of the cyclopropene derivatives gave either arylpropiolate esters or arylpropiolate orthoesters (in the presence of added amine base).The arylpropiolates can be converted to unsymmetrical 1,4-pentadiyn-3-ones by two different approaches.The first approach involved reduction of the arylpropiolate esters with diisobutylaluminum hydride to give the corresponding propargyl alcohol.Pyridinium chlorochromate or manganese dioxide oxidation of the alcohol gave the propargyl aldehydes.Addition of a lithium acetylenide gave a 1,4-pentadiyn-3-ol, which could then be oxidized to the 1,4-pentadiyn-3-one with 10percent chromic acid or manganese dioxide.The second pathway used a Lewis acid mediated coupling of a propargylic acid chloride with a (trimethylsilyl)acetylene to give the 1,4-pentadiyn-3-ones directly.The coupling of 2-thiophenepropiolic acid chloride gave the product of HCl addition to the expected 1,4-diynone.The regiochemistry of addition was determined to be chloride addition to the thiophene-bearing triple bond on the basis of 1H NMR studies.The diynones were converted to unsymmetrical 2,6-disubstituted tellura-4H-pyran-4-ones with disodium telluride anion.