Synthesis of Isoindoles via 1,3-Dipolar Cycloaddition of α-Azido Carbonyl Compounds onto Intramolecular Alkenes and Their Conversion into Substituted Aromatic Hydrocarbons

alpha-Azido carbonyl compounds bearing a 2-alkenylaryl moiety in the a-position are found to be promising precursors in the synthesis of isoindoles via 1,3-dipolar cycloaddition of azides to alkenes. Applications of these isoindoles in the preparation of 1,2,3,4-tetrasubstituted naphthalene and 9,10-disubstituted anthracene derivatives were developed via [4+ 2]-cycloaddition reactions of isoindoles with dimethyl acetylenedicarboxylate and benzynes, respectively, followed by deaminative aromatization.