Journal
JOURNAL OF ORGANIC CHEMISTRY
Volume 81, Issue 15, Pages 6808-6815Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acs.joc.6b01072
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Funding
- NSF [RUI: 1362813]
- Hobart and William Smith Colleges
- Patchett Family
- Direct For Mathematical & Physical Scien
- Division Of Chemistry [1362183] Funding Source: National Science Foundation
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A simple and flexible approach to 3-pyrrolin-2-one fused carbazoles is disclosed. The key step involves the BF3-mediated electrophilic substitution of indoles with N-alkyl-substituted 3-aryltetramic acids, which provides access to indole-substituted 3-pyrrolin-2-ones. Scholl-type oxidative cyclizations of these materials led to the formation of the corresponding 3-pyrrolin-2-one-fused benzo [a]carbazoles and indolo[2,3-a]carbazoles. This work represents the first synthesis of the benzo [a]pyrrolo[3,4-c]carbazol-3(8H)-one ring system, while the indolo[2,3-a]pyrrolo[3,4-c]carbazol-5-one ring system is found in a number of biologically active compounds including the protein kinase C (PKC) inhibitor, staurosporine.
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