Palladium/silver co-catalyzed tandem reactions synthesis of phenylacetophenone derivatives by oxabenzonorbornadienes with terminal alkynes and their anti-tumor or anti-cancer activities

A method of synthesizing a compound having a structure of formula (I) or formula (II):

• wherein each of R1, R2, R3, R4 is selected from a group consisting of H, OH, OCH2CH2O, OCH2O, OCF3, CF3, CH2CH2OH, aryl, aryloxyl, halogen, alkyl, alkenyl, alkynyl, hydroxyl, alkoxyl, amine and nitro groups, among them one of OCH2CH2O and OCH2O is substituted between R1 and R2, or R2 and R3, or R3 and R4, and
• wherein each of R5, R6, R7, R8, R9 is selected from a group consisting of H, OH, OCH2CH2O, OCH2O, OCF3, CF3, CH2CH2OH, aryl, aryloxyl, halogen, alkyl, alkenyl, alkynyl, hydroxyl, alkoxyl, amine, nitro, nitrile, alkylthio, alkyl sulfonyl, and aryl sulfonyl groups, among them one of OCH2CH2O and OCH2O is substituted between R1 and R2, or R2 and R3, or R3 and R4,
• comprising steps of:
• adding a Pd complex, a ligand and a first solvent in a first noble gas atmosphere to form a first mixture;
• stirring the first mixture at a first given temperature for a first given time duration;
• adding CF3SO3Ag to the stirred first mixture to form a second mixture;
• stirring the second mixture for a second given time duration;
• adding an oxobenzonorbornadiene derivative and a second solvent to the stirred second mixture to form a third mixture;
• stirring the third mixture for a third given time duration;
• adding a terminal alkyne to the third mixture to form a fourth mixture;
• stirring the fourth mixture in a second noble gas atmosphere at a second given temperature until the complete consumption of the oxobenzonorbornadiene derivative;
• evaporating the solvents in the stirred fourth mixture to obtain residue;
• and
• purifying the residue to obtain the compound;
• wherein the oxobenzonorbornadiene derivative is of a structure of formula (III):
• wherein R1 is selected from a group consisting of H, OMe, Me, OCH2CH2O, OCH2O, Ph, and OPh;
• R2 is selected from a group consisting of H, Me, Br, Cl, F, OCH2, OMe, OCH2CH2O, OCH2O, Ph, and OPh;
• R3 is selected from a group consisting of H, Me, Br, Cl, F, CH2O, O, OMe, OCH2CH2O, OCH2O, Ph, and OPh;
• and R4 is selected from a group consisting of H, OMe, Me, OCH2CH2O, OCH2O, Ph, and OPh;
• and
• wherein the terminal alkyne is of a structure of formula (IV):
• R1—≡—R2 (IV),
• wherein R1 is selected from a group consisting of H and D;
• and R2 is selected from a group consisting of Ph, 3-MeOC6H4 3,5-diMeOC6H3, 4-FC6H4 4-PhOC6H4, 4-CF3OC6H4, 4-BrC6H4, 4-MeC6H4, 4-OHCH2C6H4, 4-CF3C6H4, and 4-CNC6H4.