A domino synthetic strategy leading to two-carbon-tethered fused acridine/indole pairs and fused acridine derivatives?

Organic & Biomolecular Chemistry Pub Date: 2012-09-07 DOI: 10.1039/C2OB26315G

Abstract

A series of new poly-functionalized two-carbon-tethered fused acridine/indole pairs were synthesized via Br?nsted acid-promoted domino reactions between indoline-2,3-dione and C2-tethered indol-3-yl enaminones. The reactions were further expanded to prepare C-tethered fused acridine/pyridine pairs, N-substituted amino acids, N-cyclopropyl and N-aryl substituted fused acridine derivatives, as well as bis-furan-3-yl-substituted indoles. During these reaction processes, the domino construction of a fused acridine skeleton with concomitant formation of two new rings was readily achieved in a one-pot operation. The procedures are facile, avoiding time-consuming and costly syntheses, tedious work-up and purification of precursors.

Graphical abstract: A domino synthetic strategy leading to two-carbon-tethered fused acridine/indole pairs and fused acridine derivatives
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