

HETEROCYCLES BASED ON 1-((Z)-1,4-DIBROMOBUT-2-EN-2-YL)ADAMANTANE

Abstract
The possibility of constructing various N-, S-, O-containing heterocyclic systems based on the transformations of 1-((Z)-1,4-dibromobut-2-en-2-yl)adamantane was shown. Adamantyl-containing pyrrolines, pyrroles, pyridazinium salt, furan, thiophene, (dihydro)-1,6-benzodioxocine, diazocine, oxazocine, thiazocine were synthesized. It was found that the dihydro derivatives formed as a result of the reactions are unstable and can be easily oxidized by atmospheric oxygen to the corresponding heteroaromatic compounds.
Keywords
adamantane; allyl halides; cage compounds; 1,4-diazocine; 1,4-dioxocine; furan; pyrrolines; Diels–Alder reaction; heterocyclization reactions; oxidation.
Latvian Institute of Organic Synthesis - Aizkraukles iela, 21, Riga, LV-1006, Latvia - hgs@osi.lv