Journal
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
Volume 2022, Issue 24, Pages -Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/ejoc.202200364
Keywords
Ellipticine; Methylcarbazoles; Microwave chemistry; 4-Oxazolin-2-ones; Palladium
Categories
Funding
- SIP/IPN [20200227, 20210700, 20221003, 20220900]
- CONACYT [A1-S17131, 282033, 300520]
- Secretaria de Investigacion y Estudios Avanzados/UAEMex [4512/2018/CI]
- SIP/IPN (BEIFI)
- Ludwig K. Hellweg Foundation
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New and efficient strategies for the conversion of 4-oxazolin-2-ones into 1-methyl and 1,4-dimethyl 3-formylcarbazoles are described. The diarylamines were obtained in high overall yields through highly convergent cascade and one-pot processes. The synthesis of methylated carbazoles by reacting 4,5-dimethyl-4-oxazolin-2-ones with enones under microwave irradiation was given special attention. The carbazole scaffold was provided by the palladium(II)-catalyzed double C-H activation to generate oxidative cyclization of diarylamines. This methodology allowed for formal total syntheses of four naturally occurring pyrido[4,3-b]carbazole alkaloids ellipticine, 9-methoxyellipticine, olivacine, and 9-methoxyolivacine.
New and efficient strategies for the conversion of 4-oxazolin-2-ones into 1-methyl and 1,4-dimethyl 3-formylcarbazoles are herein described. Highly convergent cascade and one-pot processes afforded the corresponding diarylamines, as in situ formed synthetic intermediates or final products in high overall yields. Special attention was given to the synthesis of methylated carbazoles by reacting 4,5-dimethyl-4-oxazolin-2-ones with enones under microwave irradiation. The carbazole scaffold was provided by the palladium(II)-catalyzed double C-H activation to generate oxidative cyclization of diarylamines. This methodology allowed for formal total syntheses of four naturally occurring pyrido[4,3-b]carbazole alkaloids ellipticine, 9-methoxyellipticine, olivacine, and 9-methoxyolivacine.
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