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Regioselective synthesis of 2-methyl-2,5,6,11,12,13-hexahydro 4H indazolo[5,4-a]pyrrolo[3,4-c]carbazole-4-ones
✍ Scribed by Ming Tao; Chung Ho Park; Kurt Josef; Robert L. Hudkins
- Publisher
- Journal of Heterocyclic Chemistry
- Year
- 2009
- Tongue
- English
- Weight
- 109 KB
- Volume
- 46
- Category
- Article
- ISSN
- 0022-152X
- DOI
- 10.1002/jhet.200
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✦ Synopsis
Abstract
magnified image 2‐Methyl‐2,5,6,11,12,13‐hexahydro 4H indazolo[5,4‐a]pyrrolo[3,4‐c]carbazole‐4‐one was synthesized utilizing a regioselective Diels‐Alder reaction with 5‐(1H‐indol‐2‐yl)‐2‐methyl‐6,7‐dihydro‐2H‐indazole and ethyl cis‐β‐cyanoacrylate. Acetic acid and YtBr~3~ were the best solvent and catalyst for the regioselective Diels‐Alder reaction. The chemistry was used to synthesize novel 8‐pyrimidinyloxy‐2,5,6,11,12,13‐hexahydro 4H indazolo[5,4‐a]pyrrolo[3,4‐c]carbazole‐4‐ones that were screened and found to be potent inhibitors of DLK. J. Heterocyclic Chem., (2009).
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