| Autor: |
Osipov DV; Samara State Technical University, 244 Molodogvardeyskaya St., Samara 443100, Russian Federation., Demidov MR; Samara State Technical University, 244 Molodogvardeyskaya St., Samara 443100, Russian Federation., Artemenko AA; Samara State Technical University, 244 Molodogvardeyskaya St., Samara 443100, Russian Federation., Rashchepkina DA; Samara State Technical University, 244 Molodogvardeyskaya St., Samara 443100, Russian Federation., Krasnikov PE; Samara State Technical University, 244 Molodogvardeyskaya St., Samara 443100, Russian Federation., Osyanin VA; Samara State Technical University, 244 Molodogvardeyskaya St., Samara 443100, Russian Federation. |
| Abstrakt: |
Various substituted pyrrolo[1,2- a ]quinolines and pyrrolo[2,1- a ]isoquinolines were synthesized in good to high yields by the Et 3 N-mediated reaction of push-pull 3-nitrobenzofurans or 1-Ts-/1-Ms-3-nitroindoles and precursors of carbonyl-stabilized quinolinium and isoquinolinium ylides as 1,3-dipole equivalents. These transformations proceed in a one-pot manner starting with the formal [3 + 2]-cycloaddition stage, which is accompanied by double dearomatization of both quinoline/isoquinoline and benzofuran/indole moieties, followed by ring-opening of cyclic intermediate formed and nitrous acid elimination sequence. [3 + 2]-Cycloadducts were isolated as the final products in cases of impossibility or difficulty of their enolization. The present protocol was successfully extended to 3-nitro-4 H -chromene derivatives as push-pull dipolarophile component. Finally, using the method of competing reactions, the reactivity of the starting compounds was compared with each other. |
