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Title
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Synthesis of 6-methyl-6**H**-indolo[3,2-**c**]isoquinoline and 6-methyl-6**H**-indolo[2,3-**c**]isoquinoline: two new unnatural isoquinoline isomers of the cryptolepine series
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Author
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Abstract
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| 11H-indolo[3,2-c]isoquinoline has been synthesized in two steps starting from 4-bromoisoquinoline and 2-bromoaniline via a selective BuchwaldHartwig 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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Language
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English
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Source (journal)
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Tetrahedron. - Oxford, 1957, currens
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Publication
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Oxford
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2008
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ISSN
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0040-4020
[print]
1464-5416
[online]
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DOI
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10.1016/J.TET.2008.08.116
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Volume/pages
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64
:51
(2008)
, p. 11802-11809
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ISI
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000261714100037
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Full text (Publisher's DOI)
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Full text (publisher's version - intranet only)
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