Metal Triflate Mediated Synthesis of Selected Biologically Active Heterocyclic Compounds

Abstract

The thesis entitled Metal triflate mediated synthesis of selected biologically active heterocyclic compounds newlinedeals with the synthesis of some selected bioactive heterocyclic compounds using metal triflates as catalyst newlineunder mild reaction conditions The synthesized compounds have been evaluated for cSrc kinase inhibition newlineanticancer activities andor antimicrobial activities The thesis is divided in four chapters newlineThe first chapter of thesis describes the use of ytterbium triflate immobilized in bmimBF4 ionic liquids in newlinethe synthesis of tetrahydroindazolones 67 flavanone 74 and dihydroquinolinones 81 The chapter is divided in newlinetwo parts In partA an environmentally benign regioselective synthesis of tetrahydroindazolones was newlinedeveloped by threecomponent condensation reaction of 13diketones 60 aryl hydrazines 62 and aryl newlinebenzaldehydes 61 using YbOTf3 as a catalyst in bmimBF4 ionic liquid An array of 33 compounds was newlineprepared in good yields 48 88 and evaluated for inhibition of cell proliferation of HT29 SKOV3 and newlinecSrc kinase inhibitory activity Compounds 67ada and 67aaj has shown moderate cSrc kinase inhibition newlinewith IC50 values of 351 and 507 and#956;M respectively while compound 67bab inhibited cell proliferations of SKOV newline3 and HT29 cells by 62 and 58 respectively at 50 and#956;M In partB of the chapter an efficient and newlineenvironmentally benign method was developed for the synthesis of 2arylchroman4one flavanone 74 and newline2aryl23dihydroquinolin41Hones dihydroquinolinone 81 by the isomerization of 2and#42892;hydroxychalcone newlineand 2and#42892;aminochalcone using YbOTf3 as Lewis acid catalyst in bmimBF4 ionic liquid newlineThe second chapter of thesis briefly describes metal triflate catalyzed organic reaction under microwave newlineirradiation In partA microwaveassisted and InOTf3mediated hydroarylation of and#946;naphthols 42 and newlinealkynes 44 gave and#945;hydroxy styrenes vinylnaphthols 49 which were further treated with PdOAc2 and aryl newlineiodide 47 to give 23diarylnaphthofurans in moderate to good 3672 yield In partB a microwave newlineassisted and YbOTf3 catalyzed method was developed for the synt