1485-19-4Relevant articles and documents
Intramolecular Ritter reactions of 2-(2-cyanoethyl)tetrahydrocyclopenta-[b] indole and -carbazole derivatives
Maertens, Faye,Van Den Bogaert, An,Compernolle, Frans,Hoornaert, Georges J.
, p. 4648 - 4656 (2004)
Intramolecular Ritter reactions of 2-(2-cyanoethyl)tetrahydrocyclopenta[b] indole and -carbazole derivatives, prepared by a sequence of two different α-substitutions and Grignard reactions of the indole-based ketones 4-methyl-1,4-dihydrocyclopenta[b]indol-3(2H)-one and 9-methyl-2,3,4,9- tetrahydro-1H-carbazol-1-one, were used as key steps in the construction of various tetracyclic lactam compounds. Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2004.
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Ruberg,Small
, p. 1591 (1938)
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Two-Carbon Ring Expansion of Cyclobutanols to Cyclohexenones Enabled by Indole Radical Cation Intermediate: Development and Application to a Total Synthesis of Uleine
Leclair, Alexandre,Wang, Qian,Zhu, Jieping
, p. 1209 - 1215 (2022/01/19)
A single-electron transfer (SET) oxidation of indole or benzo[b]thiophene to a radical cation reverses the intrinsic polarity of these π-excessive bicyclic heteroarenes. Here we report an oxidative two-carbon homologation of cyclobutanols to cyclohexenones under a visible-light photoredox catalysis. 1-(Indol-2-yl)cyclobutan-1-ols are converted to 2,3,4,9-tetrahydro-1H-carbazol-1-ones, important structural motifs found in alkaloids and pharmaceuticals, with a broad substrate scope. A mechanistic study suggests that the reaction is initiated by an SET from an indole to an excited acridinium salt to generate the radical cation, which is followed by two consecutive 1,2-alkyl migrations and a rearomatization. Benzo[b]thiophene-substituted cyclobutanols are similarly converted to 2,3-dihydrodibenzo[b,d]thiophen-4(1H)-ones. A total synthesis of (±)-uleine featuring this ring-expansion process is documented.
A novel necroptosis inhibitor - Necrostatin-21 and its SAR study
Wu, Zhijie,Li, Ying,Cai, Yu,Yuan, Junying,Yuan, Chengye
supporting information, p. 4903 - 4906 (2013/09/02)
An initial structure-activity relationship study of the novel necroptosis inhibitor Nec-21 was described. Any changes of the tetracyclic scaffold were detrimental for the activity. Introduction of a substituent to 7 or 8 position (e.g., cyano or methoxy group, respectively), would increase the activity. The 7 and 8-position disubstituted compound 17b was 35-fold as potent as the lead, while EC50 reached 14 nM.