Palladium-Catalyzed Double Reductive Cyclization of 2,3-Dinitro-1,4-dialkenylbenzenes. Synthesis of 1 H ,8 H -Pyrrolo[3,2- g ]indoles.

Autor: Ansari NH; C. Eugene Bennett Department of Chemistry, West Virginia University, Morgantown, West Virginia 26506-6045, United States., Banini S; C. Eugene Bennett Department of Chemistry, West Virginia University, Morgantown, West Virginia 26506-6045, United States., Cummings MM; C. Eugene Bennett Department of Chemistry, West Virginia University, Morgantown, West Virginia 26506-6045, United States., Söderberg BCG; C. Eugene Bennett Department of Chemistry, West Virginia University, Morgantown, West Virginia 26506-6045, United States.
Jazyk: angličtina
Zdroj: The Journal of organic chemistry [J Org Chem] 2020 Mar 20; Vol. 85 (6), pp. 4002-4010. Date of Electronic Publication: 2020 Mar 06.
DOI: 10.1021/acs.joc.9b03290
Abstrakt: A flexible route to both symmetrical and unsymmetrical 1 H ,8 H -pyrrolo[3,2- g ]indole has been developed. The key and ultimate step is a double palladium-catalyzed, carbon monoxide mediated reductive cyclization of 1,4-dialkenyl-2,3-dinitrobenzenes. The cyclization precursors were prepared by a double Kosugi-Migita-Stille cross coupling of 1,4-dibromo-2,3-dinitrobenzene with an alkenyltin reagent to give symmetrical products. Unsymetrical cyclization precursors were prepared by two sequential cross couplings using 4-iodo-2,3-dinitrophenyl trifluoromethanesulfonate as the starting material.
Databáze: MEDLINE