Title
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 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
Author
Faculty/Department
Faculty of Sciences. Chemistry
Publication type
article
Publication
Oxford ,
Subject
Chemistry
Source (journal)
Tetrahedron. - Oxford
Volume/pages
64(2008) :51 , p. 11802-11809
ISSN
0040-4020
ISI
000261714100037
Carrier
E
Target language
English (eng)
Full text (Publishers DOI)
Affiliation
University of Antwerp
Abstract
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.
E-info
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