Construction of Benzo[c]carbazoles and Their Antitumor Derivatives through the Diels–Alder Reaction of 2-Alkenylindoles and Arynes
- 3 August 2015
- journal article
- research article
- Published by American Chemical Society (ACS) in The Journal of Organic Chemistry
- Vol. 80 (16), 8122-8133
- https://doi.org/10.1021/acs.joc.5b01223
Abstract
The direct assembly of benzo[c]carbazole derivatives via the Diels-Alder reaction of arynes and easily accessible 2-alkenylidoles was reported. By employing different aryne precursor loads, 6,7-dihydrobenzo[c]carbazoles or aryl-substituted 7,11b-dihydrobenzo[c]carbazoles could be controllably generated in good to excellent yields under a nitrogen atmosphere. On the other hand, when the reaction was conducted under oxygen, oxidated/aromatized product benzo[c]carbazoles could be generated directly with high selectivity and efficiency in a one-step manner. Interestingly, the benzo[c]carbazole-5-carboxamide amidation derivatives of the above products showed good antitumor activities. The inhibitory effect of these molecules against cancer cells was also described.Keywords
Funding Information
- Fundamental Research Funds for the Central Universities
- National Natural Science Foundation of China (21102043)
This publication has 75 references indexed in Scilit:
- Multicomponent Reactions Involving Arynes, Quinolines, and AldehydesOrganic Letters, 2013
- A Closer Look at Aryne Chemistry: Details that Remain MysteriousAsian Journal of Organic Chemistry, 2013
- The hexadehydro-Diels–Alder reactionNature, 2012
- Aryne Insertion into I–I σ-BondsOrganic Letters, 2012
- Arynes in Transition‐Metal‐Free Multicomponent Coupling ReactionsAngewandte Chemie, 2012
- Reaction of Arynes with Carbon-Heteroatom Double BondsHETEROCYCLES, 2012
- Intermolecular C−O Addition of Carboxylic Acids to ArynesOrganic Letters, 2010
- Highly Efficient Route to Fused Polycyclic Aromatics via Palladium-Catalyzed Aryne Annulation by Aryl HalidesThe Journal of Organic Chemistry, 2006
- Palladium-Catalyzed Controlled Carbopalladation of BenzyneJournal of the American Chemical Society, 2000
- Reactivity and decay pathways of photoexcited anilinonaphthalenesJournal of the American Chemical Society, 1982