Orthogonal Synthesis of Isoindole and Isoquinoline Derivatives from Organic Azides

Abstract

Alpha-azido carbonyl compounds bearing a 2-alkenylaryl moiety at the alpha-position are found to be promising precursors for synthesis of isoindole and isoquinoline derivatives via 1,3-dipolar cycloaddition of azides onto alkenes and 6pi-electrocyclization of N-H imine intermediates, respectively.

Gold-catalyzed regioselective oxidation of terminal allenes: formation of α-methanesulfonyloxy methyl ketones

“…It is of note that α-methanesulfonyloxy ketones are versatile synthetic intermediates that can undergo various reactions [27], including substitution [28], elimination [29], the formation of zinc homoenolates [30], the formation of cyclopropane rings under photo-irradiation [31–33], the formation of aminoimidazoles [34], the generation of cyclopropanone–oxyallyl intermediates [35], and ring contraction [36]. Their direct synthesis from corresponding ketones can be realized via oxidation by using either CuO/MsOH [37–38] or PhI(OH)OMs [39].…”

Application of Organic Azides for the Synthesis of Nitrogen-Containing Molecules

“…19b aAryl-substituted vinyl azides reacted smoothly to afford the corresponding pyrroles in good yields (entries 1-9). Tetrasubstituted pyrrole 87 could be synthesized from 2-methyl-1-phenylvinyl azide (62) in good yield (entry 9). The reaction of 2-pyrrolylvinyl azide 52 gave bipyrrole 88 in 68% yield (entry 10).…”

“…62 The reaction could also be used to install methyl and benzyl groups, as well as some cycloalkyl moieties and an alkene tether, at the C-3 position of the isoindole (entries 2-8). The reaction of azide 344 bearing a 4-toluoyl group instead of ethoxycarbonyl also proceeded smoothly to give 1-toluoylisoindole 345 in 85% yield (entry 9).…”

Comprehensive Strategies for the Synthesis of Isoquinolines: Progress Since 2008

“…Azides undergo 1,3‐dipolar cycloaddition on to alkene followed by 6π‐electrocyclization of N−H intermediates results in corresponding isoquinoline derivative 444 a (Scheme 276). [36c] …”