One-Pot Synthesis of Functional 2,3-Dihydrobenzoselenophenes and Selenochromanes from Acetyleugenol and Selenium Dibromide. Rearrangement of 2-Bromomethyl2,3-dihydrobenzoselenophene to Selenochromanes
Effective methods for the synthesis of new condensed heterocyclic compounds based on the reactions of annulation-functionalization of acetyleugenol with selenium dibromide have been developed. The methods allow one-pot preparation of functional derivatives of dihydrobenzoselenophene and selenochromane having bromo, methoxy and acetoxy groups. A rearrangement in the reactions of nucleophilic substitution of bromine in 2-(bromomethyl)-6-hydroxy-5-methoxy-2,3-dihydrobenzoselenophene, which proceeds with the expansion of the ring and the formation of selenochromane derivatives, was found.