Solid-Phase Synthesis of Heterocycles with α-Haloketones as the Key Building Blocks

Abstract

This short review summarizes the use of α-haloketones in the preparation of various heterocycles with the application of solidphase synthesis. A literature survey revealed that eighteen different five-to-seven membered scaffolds are accessible, including condensed heterocycles and bisheterocycles. 22 Conclusion Key words α-haloketones, heterocycles, rearrangement, solid-phase synthesis, cyclization Miroslav Soural (left) was born in Olomouc, Czech Republic, in 1978. He studied chemistry at Palacky University, Olomouc, where he also received his Ph.D. in organic chemistry (in 2006). After his postdoctoral fellowship at the University of Notre Dame (USA), he was appointed Associated Professor at Palacky University, Olomouc. From 2012 he has held the position of Senior Researcher at the Institute of Molecular and Translational Medicine. His field of interest is the development of strategies for the solid-phase synthesis of various pharmacologically promising substances with the emphasis on heterocyclic chemistry. Veronika Fülöpová (right) was born in Opava, Czech Republic, in 1985. During her graduate studies at Palacky University, Olomouc (Czech Republic) she became an investigator on several student grant projects regarding the solid-phase synthesis of novel heterocyclic compounds. After defending her Ph.D. thesis devoted to nitrobenzenesulfonamide chemistry, she received her Ph.D. degree in 2015 from the same university. Currently, she is working as a researcher at the Institute of Molecular and Translational Medicine in Olomouc, and the main area of her interest is solution-/solid-phase synthesis of nitrogenous heterocycles with potential biological activity.

Rapid and General Access to α-Haloketones Using Quaternary Ammonium Salts as Halogen Sources

“…α-Halogenated ketones are unique structural units found in natural products and are valuable synthetic intermediates for functional heterocycle molecules preparation. − A significant body of work has been dedicated to the design and development of new synthetic protocols to access haloketones, and most of these processes have been reviewed in the literature. − The major protocols include direct α-halogenation of aryl ketones, oxyhalogenation of hydrocarbons or secondary alcohols, and Friedel–Crafts acylation of corresponding aromatic hydrocarbons with haloacetyl halides. − . Importantly, the commonly used halogenating agents are halogens and HX or N-haloamides.…”