Alkylation of Azole Derivatives

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Table of Contents

Introduction………………………………………………………………………..

Background…………………………………………………………………………

Previous Work……………………………………………………………………

Results and Discussion……………………………………………………………

Future Work………………………………………………………………………..…

Experimental Procedures………………………………………………………………

References………………………………………………………………………………

Introduction

Synthesis of molecules is very important in the development of natural products used in medicine today.1 However, there are many problems with the current synthesis method that conflict with many of the guidelines in the 12 Principles of Green Chemistry and are potentially hazardous.2 The proposed research plan includes the formation of a salt by allylation followed by the Aza-Claisen rearrangement which has shown success using benzothiazole. Ultimately, this research seeks to eliminate these costly, inefficient factors and create a more productive, safer plan to achieve the natural products used in medicine today.

Azoles are 5-membered ring heterocycles containing a nitrogen atom and at least one other non-carbon atom.

Azole derivatives are most frequently found in medicines that treat fungal infections. Some very common examples are fluconazole, miconazole, and ketoconazole which work by inhibiting cytochrome P450-dependent enzymes that are part of ergosterol synthesis within the cell membrane.3

Azoles can also be found in medication that treats AIDS, cancer, and acid reflux disease. The synthesis of azole derivatives is a key step in acquiring the compounds used in these drugs; and because azoles are widely used in today’s society, it is important to make this process as efficient as possible.

Over the past few decades, people in our society have become much more aware o...

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...ecent Advances in Carbon–Carbon Bond-Forming Reactions Involving Homoenolates Generated by NHC Catalysis. Nair, V.; Vellalath, S.; Babu, B. P. Chem. Soc. Rev. 2008, 37, 2691-2698.

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