Description
Research areas
Synthesis of organofluorine compounds
Development of methodology for organic synthesis based on fluorine, silicon and organoboron compounds
Development of methods for the formation of communication C-C
Main results
Development of new methods for nucleophilic fluoroalkylation
Field of study
study of the reactivity of nitro compounds and their derivatives (acyclic and cyclic nitronates), directed synthesis of functional compounds from aliphatic nitro compounds.
Main results
A new strategy for the use of aliphatic nitro compounds in directional organic synthesis, based on the process of silylation, is proposed. A convenient scheme has been developed for the synthesis of the well-known highly active drug analogs Rolipram and Tsilomilast from the available precursors. This scheme is much more efficient than the synthesis of these drugs, proposed by the American company GlaxoSmithKline. For the first time, the synthesis of 1,4,6,10-tetraazaadamantanes - representatives of a new heterocyclic system isomeric urotropin.
Scheme 2
Silylation of aliphatic nitro compounds (AH) is a unique process that has no close analogies in organic chemistry. It is a kind of redox process, i.e. a chain of successive transformations of the initial AN in which the nitro group is gradually reduced under the action of mediators (silylating agents), while the carbon skeleton of the molecule, on the contrary, is oxidized. In this case, the consecutive elimination of protons from α, β, and γ of carbon atoms of molecules of initial AN is carried out. Intermediate products and intermediates of this process are the corresponding nitronates, N, N-bis-hydroxyimine cations, nitroso-acetals and conjugated en-oximes.
Scheme 3
The proposed approach allows using the same key procedure (silylation) to transform a small number of readily available AN into various polyfunctional derivatives. Many processes have high regio and stereoselectivity.
