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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
Author(s) -
Tao Ming,
Park Chung Ho,
Josef Kurt,
Hudkins Robert L.
Publication year - 2009
Publication title -
journal of heterocyclic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.321
H-Index - 59
eISSN - 1943-5193
pISSN - 0022-152X
DOI - 10.1002/jhet.200
Subject(s) - regioselectivity , chemistry , carbazole , indazole , acetic acid , catalysis , solvent , medicinal chemistry , stereochemistry , organic chemistry , combinatorial chemistry
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).