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Synthesis of the benzo-β-carboline isoneocryptolepine: the missing indoloquinoline isomer in the alkaloid series cryptolepine, neocryptolepine and isocryptolepine |
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| Authors: | Steven Hostyn Luc Pieters Péter Mátyus Roger A Dommisse |
| Institution: | a Department of Chemistry, University of Antwerp, Groenenborgerlaan 171, B-2020 Antwerp, Belgium b Department of Pharmaceutical Sciences, University of Antwerp, Universiteitsplein 1, B-2610 Antwerp, Belgium c Department of Organic Chemistry, Semmelweis University, H?gyes E. u. 7, H-1092 Budapest, Hungary d Chemical Research Center, Institute of Chemistry, Hungarian Academy of Sciences, H-1525 Budapest, P.O. Box 17, Hungary |
| Abstract: | 7H-Indolo2,3-c]quinoline has been synthesized in two steps via a new approach starting from commercially available 3-bromoquinoline and 2-bromoaniline. The new methodology consists of two consecutive palladium-catalyzed reactions: a selective Buchwald/Hartwig amination followed by an intramolecular Heck-type reaction. Alternatively, the same skeleton has also been prepared via the combination of a Suzuki arylation with an intramolecular nitrene insertion starting from 4-chloroquinoline and {2-(2,2-dimethylpropanoyl)amino]phenyl}boronic acid. Selective methylation of 7H-indolo2,3-c]quinoline yielded 5-methyl-5H-indolo2,3-c]quinoline (Isoneocryptolepine) which is an interesting new lead compound in the search for new antiplasmodial drugs. |
| Keywords: | Palladium Amination Heck-type reaction Suzuki Nitrene insertion Malaria |
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