Hypervalent Iodine as Reagent and Catalyst for The Synthesis of Bioactive Nitrogen Heterocycles

Abstract

PhD research focused on utilizing environmentally benign hypervalent iodine (HVI) reagents to facilitate organic transformation reactions. In the first chapter we have discussed how iodonium ylide (HVI) could generate carbene and radical intermediate in presence of visible light. Their utility in C-H functionalization of arenes and heteroarenes. Additionally, we have also discussed HVI reagents such as iminoiodinanes and their ability to generate nitrenes. They could also be harnessed in synthetic transformation reactions to generate numerous heterocycles. In the second chapter we have described how we have generated radicals from iodonium ylide under blue LED and subsequently used them for the functionalization of indoles and furans. In the third we have reported the [3+2] cycloaddition reactions of highly stable pyridinium ylide (generated from iodonium ylides and pyridines) with 1, 4-quinones to generate annulated indolizines via mechanochemistry. newline newlineIn the fourth chapter, we have reported a reagent free amino-pyridinylation of 1, 4-quinones by using niterenes. Nitrene could be generated photochemically from iminoiodinanes in the presence of blue LED which was then trapped by pyridine/isoquinoline to provide the amino-pyridinylated quinones. Finally, we have demonstrated the synthesis of itaconimides in the presence of a copper catalyst. Herein the pyridinium/isoquinolium ylide formed from the iodonium ylide was treated with maleimide to afford a domino sequence to provide the desired compounds.