54668-28-9Relevant academic research and scientific papers
Styrene as 4π-Component in Zn(II)-Catalyzed Intermolecular Diels-Alder/Ene Tandem Reaction
Zheng, Min,Wu, Feng,Chen, Kai,Zhu, Shifa
, p. 3554 - 3557 (2016)
A mild Zn-catalyzed intermolecular Diels-Alder/ene tandem reaction with styrene as a 4π-component is reported. A variety of dihydronaphthalene products could be prepared in moderate to good yields. Moreover, a combination of DFT calculations and experiments was performed to further understand the mechanism of this unique tandem reaction.
Regiodivergent Hydration-Cyclization of Diynones under Gold Catalysis
Mu?oz, Miguel A.,Sanz, Roberto,Solas, Marta,Suárez-Pantiga, Samuel
supporting information, p. 7681 - 7687 (2020/10/12)
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.
An Unexpected Domino Reaction of β-Keto Sulfones with Acetylene Ketones Promoted by Base: Facile Synthesis of 3(2H)-Furanones and Sulfonylbenzenes
Tong, Wei,Li, Qian-Yu,Xu, Yan-Li,Wang, Heng-Shan,Chen, Yan-Yan,Pan, Ying-Ming
supporting information, p. 4025 - 4035 (2017/11/21)
An unexpected domino reaction of β-keto sulfones with acetylene ketones has been developed. The domino reaction of β-keto sulfones with diynones proceeded smoothly in the presence of 30 mol% K2CO3 without other additives, and afforded the novel 3(2H)-furanone derivatives. On replacing the diynones with terminal alkyne ketones, the reaction regioselectivity was changed and sulfonylbenzenes were obtained via benzannulation in good yields. (Figure presented.).
Transition Metal-Free Synthesis of 3-Alkynylpyrrole-2-carboxylates via Michael Addition/Intramolecular Cyclodehydration
Teng, Qing-Hu,Xu, Yan-Li,Liang, Ying,Wang, Heng-Shan,Wang, Ying-Chun,Pan, Ying-Ming
supporting information, p. 1897 - 1902 (2016/07/06)
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.) .
Preparation of Arylpropiolate Esters from Trichlorocyclopropenium Cation and Elaboration of the Esters to Unsymmetrical 1,4-Pentadiyn-3-ones and Unsymmetrical Tellurapyranones
Wadsworth, Donald H.,Geer, Susan M.,Detty, Michael R.
, p. 3662 - 3668 (2007/10/02)
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.
