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

ABSTRACT: A flexible route to both symmetrical and unsymmetrical 1H,8H-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.

SUBMITTER: Ansari NH

PROVIDER: S-EPMC9827688 | biostudies-literature | 2020 Mar

REPOSITORIES: biostudies-literature

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

Ansari Nurul H NH Banini Serge S Cummings Matthew M MM Söderberg Björn C G BCG

The Journal of organic chemistry 20200306 6

A flexible route to both symmetrical and unsymmetrical 1H,8H-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 ...[more]

PMID: 32130856

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