100108-66-5

Usage

InChI:InChI=1/C13H9NO2/c1-7-6-10(15)12-11(13(7)16)8-4-2-3-5-9(8)14-12/h2-6,14H,1H3

Upstream product

• 14960-81-7 1-hydroxy-3-methyl-9H-carbazole 
• 4532-33-6 1-methoxy-3-methylcarbazole 
• 57675-09-9 2-methyl-5-(phenylamino)cyclohexa-2,5-diene-1,4-dione 
• 1477-50-5 Indole-2-carboxylic acid 
• 1316258-51-1 C₁₇H₁₉NO₃ 
• 1316258-56-6 C₁₇H₁₇NO₃ 
• 1316258-48-6 C₁₅H₁₅NO₃ 
• 188037-57-2 3-iodo-1-(methoxymethyl)indole-2-carboxaldehyde 
• 95-71-6 2-methylbenzene-1,4-diol 
• 62-53-3 aniline 
• 1375488-00-8 9-benzyl-(4-benzyloxy)-1-bromo-9H-carbazole-3-carbaldehyde 
• 1375487-97-0 4-hydroxy-9H-carbazole-3-carbaldehyde 
• 1375487-98-1 4-hydroxy-9H-carbazole-1-carbaldehyde 
• 1375487-99-2 1-bromo-4-hydroxy-9H-carbazole-3-carbaldehyde 

Relevant academic research and scientific papers

Palladium-Catalyzed Regioselective Synthesis of 1-Hydroxycarbazoles Under Aerobic Conditions

A palladium-catalyzed aerobic C?H amidation of N-Ts-2-amino-3′-hydroxylbiaryls has been developed to afford a diverse range of 1-hydroxycarbazoles with high regioselectivity and efficiency. This protocol benefits from operational simplicity, robustness, a

Synthesis of carbazoloquinone derivatives and their antileukemic activity via modulating cellular reactive oxygen species

Carbazoloquinone alkaloids are of great interest as privileged structures for anticancer drug molecules. The purpose of this study was to investigate the structure-activity relationships of carbazoloquinone derivatives as anticancer agents. A series of ca

Divergent Syntheses of Carbazole Alkaloids

Starting from common intermediate methyl 1-hydroxy-9 H -carbazole-3-carboxylate, synthetic routes toward murrayaquinone A, olivacine, and N -methylcalothrixin B were developed.

Concise synthesis and antiproliferative activity evaluation of ellipticine quinone and its analogs

We developed a concise protocol for the synthesis of ellipticine quinone from the appropriate 3-iodoindole-2-carbaldehydes in four steps. The key step is the construction of carbazole-1,4-quinone through tandem Ring-Closing Metathesis (RCM) and dehydrogen

Exploiting Alkylquinone Tautomerization for the Total Synthesis of Calothrixin A and B

The pentacyclic alkaloid calothrixin B (1) has been synthesized in 5 steps from murrayaquinone A (9). The key step involved the union of boryl aniline 31 with brominated murrayaquinone A (26). In this transformation, alkylquinone 26 undergoes tautomerization to a quinone methide, which is intercepted by boryl aniline 31 to forge a new C-N bond. An intramolecular Suzuki coupling, followed by dehydrogenative aromatization, completed the synthesis of calothrixin B. Subsequent N-oxidation of calothrixin B delivered calothrixin A. The successful synthesis of these alkaloids and the challenges that led to the development of the final synthesis plan are reported herein.

Short synthesis of carbazole alkaloids: Ekeberginine, murrayaquinone A, and glycozoline

Three differently substituted, naturally occurring, biologically active carbazole derivatives (viz. ekeberginine, murrayaquinone A, and glycozoline) were synthesized in good yield using short and simple routes. The prenyl group was selectively introduced at the C4 position using a Stille coupling reaction in the synthesis of ekeberginine. Murrayaquinone A was synthesized using Raney nickel–mediated desulfurization of dithiane as a key step. Synthesis of glycozoline was achieved in two steps from 3-methyl carbazole via an intermediate 3-bromo-6-methyl carbazole.

Concise synthesis of carbazole-1,4-quinones and evaluation of their antiproliferative activity against HCT-116 and HL-60 cells

We report a convenient synthesis of carbazole-1,4-quinone alkaloid koeniginequinones A and B using a tandem ring-closing metathesis with the dehydrogenation reaction sequence under an O2 atmosphere as an important step. Using this method, carbazole-1,4-quinones substituted at the 5-, 6-, 7-, and/or 8-positions have been synthesized. Moreover, 24 compounds, including koeniginequinones A and B, have been evaluated for their antiproliferative activity against HCT-116 and HL-60 cells, and the 6-nitro analog exhibited the most potent activity against both tumor cell types.

Synthesis of Carbazolequinones by Formal [3 + 2] Cycloaddition of Arynes and 2-Aminoquinones

A formal cycloaddition reaction for the synthesis of biologically and pharmaceutically important carbazolequinones via the annulation of aminoquinones with arynes has been developed. This practical and metal-free cascade reaction proceeds through successive C-C/C-N bond formations. Moreover, this novel method has been utilized for the concise synthesis of bioactive murrayaquinone A and koeniginequinone B and their analogues.

Palladium mediated intramolecular multiple C-X/C-H cross coupling and C-H activation: Synthesis of carbazole alkaloids calothrixin B and murrayaquinone A

Straightforward palladium mediated syntheses of calothrixin B and murrayaquinone A are described. Regioselective palladium mediated intramolecular multiple C-X/C-H cross coupling reaction on N-(4-((2-bromophenyl)amino)-2,5- dimethoxybenzyl)-N-(2-iodophenyl)acetamide followed by CAN oxidation afforded calothrixin B in excellent yield in two steps. A linear synthesis has also been developed for calothrixin B. Utilizing C-H functionalization as well as palladium mediated intramolecular C-X/C-H cross coupling reaction, murrayaquinone A synthesis was achieved. Overall, these synthetic methodologies provide an expedient entry to these biologically active alkaloids in a short reaction sequence. This journal is the Partner Organisations 2014.

Synthesis of murrayaquinone A and analogues via ring-closing C-H arylation

A compact synthesis of Murrayaquinone A is reported, based on sequential Buchwald-Hartwig amination/annulative C-H activation followed by oxidation of the intermediate carbazole. The methodology can be readily extended to other analogues with electron-rich quinone rings.