Synthesis of 6-methyl-6H-indolo[3,2-c]isoquinoline and 6-methyl-6H-indolo[2,3-c]isoquinoline: two new unnatural isoquinoline isomers of the cryptolepine series |
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Authors: | Gitte Van Baelen,Guy L.F. Lemiè re,Roger Dommisse,Koen Augustyns,Luc Pieters |
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Affiliation: | a Department of Chemistry, University of Antwerp, Groenenborgerlaan 171, B-2020 Antwerp, Belgium b Department of Biomedical Sciences, University of Antwerp, Groenenborgerlaan 171, B-2020 Antwerp, Belgium c Department of Pharmaceutical Sciences, Universiteitsplein 1, B-2610 Wilrijk, Belgium |
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Abstract: | 11H-indolo[3,2-c]isoquinoline has been synthesized in two steps starting from 4-bromoisoquinoline and 2-bromoaniline via a selective Buchwald-Hartwig reaction followed by a Pd-catalyzed intramolecular direct arylation involving C(sp2)-H activation. The synthesis of 7H-indolo[2,3-c]isoquinoline was achieved by a combination of a Suzuki reaction with an intramolecular nitrene insertion reaction starting from 4-bromoisoquinoline and {2-[(2,2-dimethylpropanoyl)amino]phenyl}boronic acid. Selective methylation of the tetracyclic skeletons yielded the title compounds 6-methyl-6H-indolo[3,2-c]isoquinoline and 6-methyl-6H-indolo[2,3-c]isoquinoline, which have never been described in the literature before. |
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Keywords: | Malaria Plasmodium falciparum Cryptolepines Palladium Buchwald-Hartwig reaction C(sp2)-H activation Suzuki reaction Nitrene insertion |
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