Development of New Synthetic Methods for the Preparation of N-functionalized Hydantoins

Abstract

Hydantoin is an organic framework of considerable chemical and biological interest as it is encountered in several drugs and natural products with biological activity. Access to synthetic tools for synthesis and modification of the hydantoin framework is therefore of importance both in academia and industry. The current synthetic methods used often include multiple steps, harsh conditions and toxic reagents, and thus have room for improvement. In this work, development of new and improved synthetic processes that allow for more efficient and less toxic production of hydantoins and derivatives is presented. The concept of the methods is direct bond formation between (carbon-based) functional groups and a specific position in the hydantoin framework. It was discovered that the key to solve this challenging task was to use copper as a catalyst. The methods developed allows for synthesis of two different classes of substituted hydantoins, including structures previously not accessible.