Selective C-7 Functionalization of Phenanthridines by Microwave-Assisted Claisen Rearrangements of 8-Allyloxyphenanthridines.

ABSTRACT: Carbon-carbon bond formation in the phenanthridine 7-position was achieved by microwave-assisted Claisen rearrangement of 8-allyloxyphenanthridines. The reactions took place with excellent regioselectivity and high chemical yields. If the 7-position was substituted, rearrangement to C-9 took place, but the reaction occurred less readily. Rearrangements of 8-allyloxy-5,6-dihydrophenanthridines (phenanthridines with a saturated B-ring) gave a mixture of 7- and 9-substituted products. The experimental results were supported by DFT (density functional theory) calculations.

SUBMITTER: Lepsoe MR 

PROVIDER: S-EPMC10362114 | biostudies-literature | 2023 Jul

REPOSITORIES: biostudies-literature