SOS Author Spotlight: Oleksandr Grygorenko and Bohdan Vashchenko (1,4-Dioxanes)

Methods for the Synthesis and Modification of 1,4-Dioxanes Compiled and Reviewed for SOS

In a recent Science of Synthesis compilation by researchers Oleksandr Grygorenko and Bohdan Vashchenko, of Kiev (Ukraine), the most useful synthetic approaches to 1,4-dioxanes are evaluated and discussed. Although the parent 1,4-dioxane is most commonly encountered as a solvent in organic synthesis, substituted 1,4-dioxanes have also been recognized as useful chemotypes in organic synthesis and drug discovery, with improved pharmacokinetics, solubility, or bioavailability of their derivatives. This scaffold can be applied for bioisosteric replacement of sp³-enriched carbo- and heterocycles, i.e. piperidine, piperazine, or morpholine, to modify the number and strength of hydrogen-bond acceptors and the overall hydrophilicity of potential drugs. Thus, molecules decorated with a 1,4-dioxane moiety are becoming more attractive for medical purposes, and a significant number of natural products and pharmaceutical agents have been disclosed.

The chapter is divided into synthetic approaches that are based on either construction of the heterocyclic core itself, or methods that introduce substituents into the parent heterocyclic structure (e.g., radical additions of 1,4-dioxanes to alkenes, or cross-coupling strategies).

The acting Volume Editor for this comprehensive review was Prof. Paul Clarke of the University of York (UK). The chapter can be accessed here on SOS.

Bohdan V. Vashchenko was born in Kyiv, Ukraine in 1995. He received a BSc (2017) and MSc (2019) in chemistry from the Taras Shevchenko National University of Kyiv. He currently a researcher at Enamine Ltd, as well as a PhD student at Taras Shevchenko National University of Kyiv. His scientific interests comprise the development of building blocks for drug discovery, including alicyclic, heterocyclic, organofluorine, and organosulfur compounds. He is the coauthor of 27 papers and a book chapter.

Prof. Dr. Oleksandr O. Grygorenko was born in Brody, Lviv region, Ukraine in 1982. He received an MS (2004), PhD (2007), and Dr.Sci. (2019) in organic chemistry from Taras Shevchenko National University of Kyiv. At present, he shares his time between his alma mater as full professor and leading researcher, and Enamine Ltd. (Kyiv, Ukraine) as consulting scientist. His scientific interests focus at the interface of organic synthesis and medicinal chemistry, including lead-oriented synthesis, organoboron, organofluorine, and organosulfur chemistry, and non-proteinogenic amino acids. Oleksandr is the coauthor of more than 170 papers and 4 book chapters.