Laboratory of new synthetic methods

Nitro compounds are among the most convenient and widely used synthons for building carbon-carbon and carbon-heteroatom bonds in organic synthesis. Their availability, as well as their high reactivity, make these compounds attractive building blocks in the synthesis of a wide variety of natural and synthetic bioactive compounds. Nevertheless, the use of nitro compounds in organic synthesis is mainly limited to their transformations, which are based on the introduction of electrophilic reagents into the α-position, the reduction of the nitro group into an amine, 1,3-dipolar cycloaddition and the Nef reaction. This circumstance, of course, narrows the scope of application of nitro compounds. In this regard, the identification of fundamentally new aspects of the reactivity of the nitro fragment, which can lead to the formation of new carbon-carbon and carbon-heteroatom bonds, is the most important direction in modern chemistry of nitro compounds. For example, the last decade has been marked by the creation of methods for reversing the traditional polarity of nitroalkanes as α-C-nucleophiles due to electrophilic activation of the nitro fragment by Brensted acids or silicon electrophiles. Currently, the interest of researchers is shifting towards the development of methods for the C-H activation of distant, inactive positions of nitroalkanes using external oxidants or the nitro group itself as an intramolecular oxidizer, as well as to search for new directions for the reaction of nitro compounds. One of our projects is primarily devoted to the development of new methodologies for the construction and C-H functionalization of heterocyclic compounds by nitroalkanes, nitroalkanes and their derivatives using electrophilic activation processes under the action of strong phosphorylating, acylating, silylating and other reagents. The process of formation of spiro isoxazoles was developed as a result of the reaction of nitroalkens with indoles, enamines and other similar compounds in phosphoric acid and methanesulfonic acid. This process represents a new type of reactivity of aliphatic nitro compounds. It allows you to obtain compounds that were previously unavailable and interesting from the point of view of biological activity. The compounds formed during these reactions have not been practically studied, despite their obvious high synthetic potential. Therefore, within the framework of this project, a comprehensive study of these substances is planned, which, it seems to us, will lead to the development of completely new synthetic methods based on aliphatic nitro compounds.