Russian chemists developed a way to synthesize drugs from renewable precursors
Scientists of RUDN University and their Russian colleagues have developed a new approach to the synthesis of benzofurans from cheap raw materials. Original furans can be produced from wastes of agriculture and woodworking industry, such as sawdust, cobs and other by-products of crop production. The results of the work were described in an article published in Tetrahedron.
Benzofuran is a heterocyclic compound consisting of fused benzene and furan rings. The last one is five-membered ring formed by four carbon atoms and an oxygen atom. Benzofuran is present in many pharmaceutical substances such as antiarrhythmic medications (Amiodarone and Dronedarone), medications for psoriasis and gout (Benzbromarone and Benziodarone), drugs for the treatment of sleep disorders (Heltioz) and skin diseases (Psoralen and Trioxalen) as well as some antidepressants. The new approach can be used for the development of new benzofuran-based drug substances.
"Original furans (N-tosylfurfurylamines) are obtained directly from agricultural or wood-processing waste, that is, from renewable sources. Biomass processing will eventually come to a serious industrial level," says Igor Trushkov, professor of organic chemistry at RUDN University.
The second component necessary for the proposed synthesis is salicyl alcohols, which are also produced commercially from a cheap precursor, that is salicylaldehyde which is obtained in one step from phenol, large-tonnage product of chemical industry. "This work is also interesting because in the reaction with salicylic alcohols, the same atom of the furan ring acts at first as a nucleophile (a reagent providing an electron pair for the formation of new bond), and then, during the same process, as an electrophile (a reagent which accepts an electron pair)," says Trushkov.
In close cooperation with a group of scientists from Perm State National Research University, led by Maxim Uchuskin, for many years Igor Trushkov has been searching for ways to synthesize heterocyclic compounds from low-cost precursors. The beginning of this field was made by Professor Alexander Butin, after whom one of the reactions was named.
More information: Anton A. Merkushev et al, A simple synthesis of benzofurans by acid-catalyzed domino reaction of salicyl alcohols with N -tosylfurfurylamine, Tetrahedron (2017).
Provided by RUDN University
