tert-butyl nitrite mediated domino synthesis of N-heterocycles via C-H bond functionalization
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2019
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Abstract
The content of his thesis has been divided into four chapters summary of which is as follows: Chapter I of the thesis presents an overview of tert-butyl nitrite mediated CH functionalization reactions and other newer strategies leading to the formation of CC and Cheteroatom bonds under metal and metal-free conditions. It mainly focused on tert butyl nitrite mediated various CH functionalization reactions viz. nitrosation, nitration, oximation, diazotization, oxidation, and construction of N-heterocycles. Chapter II describes tert-butyl nitrite mediated domino synthesis of isoxazolines and isoxazoles from terminal aryl alkenes and alkynes. An unprecedented consecutive three CH functionalizations of two styrenes are involved during this isoxazoline synthesis. In this radical mediated reaction one half of the aryl alkene is converted into intermediate 2-nitro ketone which serve as a 1,3-dipolarophile and undergo cycloaddition with the other half of unreacted aromatic terminal alkene. The use of alkyne in lieu of alkene leads to the formation of isoxazole under an identical reaction condition
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Supervisor: Bhisma K. Patel
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CHEMISTRY