Journal
SYNTHESIS-STUTTGART
Volume 49, Issue 18, Pages 4357-4371Publisher
GEORG THIEME VERLAG KG
DOI: 10.1055/s-0036-1588467
Keywords
1-and 2-oxygenated carbazoles; diarylamines; palladium(II) coupling; clausenal; clausine P
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Funding
- SIP/IPN [20150917, 20161791, 20170902]
- CONACYT [178219]
- CONACYT
- SIP/IPN (BEIFI)
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The scope and limitations of the strategy for the conversion of 2-anilinocyclohexenones and N-arylcyclohexane enaminones into the 1-and 2-oxygenated carbazole scaffolds, respectively, were evaluated. The one-pot palladium(0)-catalyzed aromatization/methylation process of the aforementioned substrates provided a diversity of the corresponding diarylamines. A subsequent palladium(II)-catalyzed cyclization of the latter delivered the desired 1-and 2-oxygenated carbazoles in good overall yields. Special attention was given to the synthesis of the uncommon 1,8-disubstituted carbazoles. This methodology was employed for the total synthesis of the naturally occurring clauraila A, clausenal, clausine P, and 7-methoxy-O-methylmukonal.
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