155200-67-2Relevant academic research and scientific papers
A Chemo- and Regioselective Tandem [3 + 2]Heteroannulation Strategy for Carbazole Synthesis: Combining Two Mechanistically Distinct Bond-Forming Processes
Burley, Glenn A.,Bush, Jacob T.,Campbell, Emma,Kennedy, Alan R.,Paisley, Olivia I.,Taladriz-Sender, Andrea
, p. 4603 - 4616 (2022/04/07)
A modular approach to prepare tri- and tetracyclic carbazoles by a sequential [3 + 2]heteroannulation is described. First, optimization of Pd-catalyzed Buchwald-Hartwig amination followed by C/N-arylation in a one-pot process is established. Second, mechanistic analyses identified the origins of chemo- and regioselective sequential control of both bond-forming steps. Finally, the substrate scope is demonstrated by the preparation of a range of tri- and tetracyclic carbazoles, including expedient access to several natural products and anti-cancer agents.
DNA intercalators. 1. Development of 2-hydroxy-benzo(b)carbazole derivatives as cytostatics
Kucklaender,Pitzler,Kuna
, p. 137 - 142 (2007/10/02)
Reaction of p-benzoquinone 3 and aminomethylene indanones 2 via easily oxidized benzocarbazoles 4/5 affords the heterocyclic quinones 6. The structure of 4/5 and 6 is proven by derivatization to 7b and 8b. The product 9 obtained by methylation of 6 is hydrogenated to 10 or debenzylated to 11. Ether cleavage yields 12. Reaction of 9 with lithium-methyl or NaBH4 affords 13 and the intermediates 14 and 15. Phenol 6a was alkylated to 16 or aminomethylated to 17 or 18. The indole quinones 17 and 18 show strong cytotoxic activity against colon cells and pulmonary carcinoma cells.
