2257-15-0

Upstream product

• 4346-59-2 para-methoxyphenyldiazonium chloride 
• 1655-07-8 ethyl 2-oxocyclohexane carboxylate 
• 3449-49-8 6-methoxy-2,3,4,9-tetrahydro-1H-carbazol-1-one 
• 823-45-0 (E)-2-(hydroxymethylene)cyclohexan-1-one 
• 104-94-9 4-methoxy-aniline 
• 823-45-0 2-(hydroxymethylene)cyclohexanone 
• 108-94-1 cyclohexanone 
• 2981-10-4 1-(cyclohex-1-en-1-yl)piperidine 

Downstream Products

• 3449-49-8 6-methoxy-2,3,4,9-tetrahydro-1H-carbazol-1-one 

Relevant academic research and scientific papers

Synthesis and Oxidative Cleavage of Oxazinocarbazoles: Atropselective Access to Medium-Sized Rings

Polycyclic systems can be converted into medium-sized-ring-containing compounds through the controlled oxidative cleavage of internal double bonds. This approach is particularly accessible in systems that contain a suitably substituted indole ring. Here, a robust approach to the synthesis of the understudied oxazinocarbazole system is reported. After regioselective incorporation of a carbonyl functional group, m-chloroperoxybenzoic acid (MCPBA) is used to cleave the indole 2,3-double bond that this system contains. This results in a competition between two processes, oxidative cleavage of the double bond and a pinacol-type rearrangement, both of which occur with very high diastereoselectivity. The balance between the two processes is studied as a function of the substrate structure. Extensive use of X-ray crystallographic analysis of the products enables detailed mechanistic conclusions to be drawn.

A novel necroptosis inhibitor - Necrostatin-21 and its SAR study

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.

Substituted tetrahydrocarbazoles with potent activity against human papillomaviruses

The synthesis and SAR of a series of substituted 1-aminotetrahydrocarbazoles with potent activity against human papillomaviruses are described. Synthetic approaches allowing for variation of the substitution pattern of the tetrahydrocarbazole are outlined and resulting changes in antiviral activity are highlighted. Several compounds with in vitro antiviral activity (W12 antiviral assay) in the low nanomolar range were identified and (1R)-6-bromo-N-[(1R)-1-phenylethyl]-2,3,4,9-tetrahydro-1H-carbazole-1-amine was selected for further evaluation.

Stereoselective formation of carbon-carbon bonds via SN2- displacement: Synthesis of substituted cycloalkyl[b]indoles

A general asymmetric synthesis of substituted cycloalkyl[b]indoles has been accomplished. The key features of this approach are (1) the utilization of a Japp-Klingemann condensation/Fischer cyclization to prepare cycloalkyl[b] indolones, (2) the asymmetric borane reduction of these heterocyclic ketones with (S)-OAB to obtain enantiomerically pure alcohols, and (3) the stereoselective SN2-displacement of these indole alcohol substrates with a carbon nucleophile under Mitsunobu conditions to set the C1 or C3 tertiary carbon stereocenter. The use of trimethylphosphine (PMe3) and bis(2,2,2-trichloroethyl) azodicarboxylate (TCEAD) was found to have an effect on the Mitsunobu dehydrative alkylation.

Tetracyclic compounds from tetrahydrocarbazolones. Part 1. Synthesis from 2,3,4,9-tetrahydrocarbazol-1-ones

Reaction of several 2,3,4,9-tetrahydrocarbazol-1-ones 1 was used to synthesise new thieno, furo and selenadiazolo annelated carbazoles.

Electrophilic Substitution in Indoles. Part 11. The Mechanism of Substitution in 5-Methoxyindoles

Deuterium labelling experiments show that the boron trifluoride-catalysed cyclisation at 90 deg C of 4-(5-methoxyindole-3-yl)butanol (1e) to 6-methoxytetrahydrocarbazole (11a) occurs by two simultaneous pathways.The main route (83.5percent) involves initial cyclisation at the 3-position of (1e) to give an intermediate spirocyclic indolenine which then rearranges to the tetrahydrocarbazole.The minor pathway (16.5percent) involves direct attack at the 2-position.A similar duality of mechanism of substitution applies to the 6-methoxy-, 4,6-dimethoxy-, and 5,6-dimethoxy-indole analogues for which the extent of substitution at the 2-position can be correlated with the calculated change in ?-electron density at the 2- and 3-positions for a series of methoxy-substituted 3-methyl-indoles.These calculations do not, however, fit the experimental findings for the 5-methoxy-derivative which appears to be anomalous, showing an unexpectedly high percentage of direct substitution at the 2-position.A possible explanation of this result is advanced.

6-Substituted-9-(2-hydroxyethyl)-1,2,3,4-tetrahydro carbazol-1-one

The present invention relates to new, pharmacologically valuable 2,4,5,6-tetrahydro-1H-pyrazino-[3,2,1-jk]-carbazoles substituted in the 8-position having the formula I STR1 wherein R stands for an alkyl or alkoxy group having 1 to 4 carbon atoms or a flu