ИСТИНА

Nucleophilic ring opening of donor-acceptor (DA) cyclopropanes is an efficient approach to various polyfunctional structures, including natural products and medicines.Currently, a wide range of nucleophiles was introduced into reactions with DA cyclopropanes; however, a number of nucleophilic reagents still remains unexplored. In this research, we have found optimal conditions for DA cyclopropanes 1 ring opening with azide ion and thus developed an efficient and reliable method for the synthesis of gamma-azidocarbonyl compounds. The presence of azide function and activated methine group in compounds makes them convenient building blocks for the streamlined synthesis of various five- and six-membered N heterocyclic frameworks which are ubiquitous structural units of numerous natural and synthetic bioactive molecules. We developed approaches to pyrrolidones, pyrroles, pyrrolines, piperideines, etc., based on simple synthetic sequences including Staudinger and aza-Wittig reactions as key steps.