Nitrones and Oxaziridines. XLIV. Synthesis of Indol-3- and -2-ylmethyl-Substituted 1-Pyrroline 1-Oxides

Abstract

3-(2'-Nitroethy1) indole (3) and more importantly 1,3-dimethyl-2-(2'-nitroethyl) indole (10) have served as precursors for the construction of several 1-pyrroline 1-oxides (6), (15) and (17) and the related 1-pyrrolines (7), (16) and (18) via the γ-nitro ketones (4): (12) and (14). Attempts to oxidize these structures to achieve highly conjugated systems were unsuccessful. X-Ray crystallographic data are presented for the 1-pyrroline 1-oxides (15) and (17).