Abstract
Bispropargyl ethers (both symmetrical and non-symmetrical) equipped with 1,4-dimethoxyaryl groups were synthesized. Under strongly basic conditions (KOBu t /toluene/reflux), these ethers underwent Garratt–Braverman type cyclization to the tetramethoxy bi-aryl systems in high yields presumably via the bisallenes. The products could be successfully converted to the bis-quinones via CAN-mediated demethylation cum oxidation. This two-step protocol offers a simple route to bis-quinones, connected by C1–C2′ bonds, in good yields. Fluorescence based EB-displacement assay, CD spectroscopy and viscosity measurements confirmed the DNA-binding ability of the synthesized quinones via intercalation.
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