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

作者：Jiang, Bo^*; Wang, Xue; Li, Meng-Yuan; Wu, Qiong; Ye, Qin; Xu, Hai-Wei; Tu, Shu-Jiang

来源：Organic and Biomolecular Chemistry, 2012, 10(42): 8533-8538.

DOI：10.1039/c2ob26315g

• ANTITUMOR POLYCYCLIC ACRIDINES
• C BOND FORMATION
• MARINE SPONGE
• ONE-POT
• MULTICOMPONENT REACTIONS
• BISINDOLE ALKALOIDS
• EFFICIENT SYNTHESIS
• CASCADE REACTION
• NATURAL-PRODUCT
• INDOLES

A series of new poly-functionalized two-carbon-tethered fused acridine/indole pairs were synthesized via Bronsted acid-promoted domino reactions between indoline-2,3-dione and C-2-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.

• 出版日期2012