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- Title
Synthesis of Diarylamines and Methylcarbazoles and Formal Total Synthesis of Alkaloids Ellipticine and Olivacine.
- Authors
Barrera, Edson; Hernández‐Benitez, R. Israel; González‐González, Carlos A.; Escalante, Carlos H.; Fuentes‐Benítes, Aydeé; González‐Romero, Carlos; Becerra‐Martínez, Elvia; Delgado, Francisco; Tamariz, Joaquín
- Abstract
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.
- Subjects
MICROWAVE chemistry; PALLADIUM; CARBONYL compounds; RING formation (Chemistry)
- Publication
European Journal of Organic Chemistry, 2022, Vol 2022, Issue 24, p1
- ISSN
1434-193X
- Publication type
Article
- DOI
10.1002/ejoc.202200364