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Usage

Uses

Used in Organic Synthesis:
(2E)-2-(phenylhydrazono)cyclohexanone is used as a building block for the synthesis of various organic compounds. Its reactivity and versatility make it a valuable component in the creation of complex molecules and pharmaceuticals.
Used in Analytical Chemistry:
(2E)-2-(phenylhydrazono)cyclohexanone is used as a reagent in analytical chemistry for the detection and determination of aldehydes and ketones. Its ability to form colored complexes with these compounds allows for their quantification in various samples.
Used in Pharmaceutical Research:
(2E)-2-(phenylhydrazono)cyclohexanone is used as a starting material in the development of new pharmaceuticals. Its potential pharmacological and biological activities have been studied, and it may contribute to the discovery of novel therapeutic agents.
Used in Colorimetric Reagents:
(2E)-2-(phenylhydrazono)cyclohexanone is used as a colorimetric reagent for the detection and quantification of aldehydes and ketones in various samples. Its color change upon reaction with these compounds provides a simple and effective method for their analysis.
Used in Chemical Industry:
(2E)-2-(phenylhydrazono)cyclohexanone is used in the chemical industry for the production of various chemicals and materials. Its versatility and reactivity make it a valuable component in the synthesis of a wide range of products.

Upstream product

• 64-17-5 ethanol 
• 127-09-3 sodium acetate 
• 100-34-5 benzene diazonium chloride 
• 1193-63-1 Cyclohexanone-2-carbaldehyde 
• 6415-38-9 benzenediazonium sulphate 
• 1655-07-8 ethyl 2-oxocyclohexane carboxylate 
• 765-87-7 cyclohexane-1,2-dione 
• 62-53-3 aniline 
• 823-45-0 2-(hydroxymethylene)cyclohexanone 
• 108-94-1 cyclohexanone 
• 18709-01-8 cyclohexanone-2-carboxylic acid 

Downstream Products

• 100983-79-7 2-{[4-(4,5,6,7-Tetrahydro-benzo[1,3]dithiol-2-ylidene)-cyclohexa-2,5-dienylidene]-hydrazono}-cyclohexanone; compound with perchloric acid 
• 1351445-87-8 2-methoxy-3-cyano-4-(2,6-dichlorophenyl)-5,6-dihydropyrido[2,3-a]carbazole 
• 1592-62-7 1-hydroxy-1,2,3,4-tetrahydrocarbazole 
• 1485-19-4 9-methyl-2,3,4,9-tetrahydro-1H-carbazol-1-one 
• 1449650-36-5 10-tosyl-2,4,5,10-tetrahydropyrazolo[3,4-a]carbazole 
• 1449650-38-7 2-methyl-10-tosyl-2,4,5,10-tetrahydropyrazolo[3,4-a]carbazole 
• 1449650-34-3 (Z)-2-(hydroxymethylene)-9-tosyl-2,3,4,9-tetrahydro-1H-carbazol-1-one 
• 1449650-33-2 9-tosyl-2,3,4,9-tetrahydro-1H-carbazol-1-one 
• 6782-77-0 cyclohexane-1,2-dione-bis-phenylhydrazone 

Relevant academic research and scientific papers

Synthesis of 2-hydroxypyrido[2,3-a]carbazoles and 2-hydroxypyrimido[4,5- a]carbazoles from 1-hydroxycarbazoles

Gattermann reaction on substituted 1-hydroxycarbazoles (4a-d) afforded substituted 1-hydroxycarbazole-2-carbaldehydes (5a-d) from which synthesis of either 2-hydroxypyrido[2,3-a]carbazoles (7a-d) via Perkin reaction or 2- hydroxypyrimido[4,5-a]carbazoles (8a-d) via condensation with urea could be achieved.

Enantioselective Synthesis of 1- and 4-Hydroxytetrahydrocarbazoles through Asymmetric Transfer Hydrogenation

Several 1- and 4-hydroxytetrahydrocarbazoles were prepared in high yields (up to 99%) and excellent enantiomeric excesses (up to >99% ee) from the corresponding 1- and 4-oxotetrahydrocarbazoles through asymmetric transfer hydrogenation by using the commercially available Noyori-Ikariya ruthenium catalyst. The immediate use of the freshly prepared catalyst and the use of a HCO 2 H-DABCO (11:6) mixture as the hydrogen source are crucial for achieving high activity and enantioselectivity. In this way, a tetrahydrocarbazole heterocycle fused to a lactone moiety was synthesized in 45% yield and 97% ee.

Total Synthesis of Olivacine and Ellipticine via a Lactone Ring-Opening and Aromatization Cascade

Effective preparation of olivacine and ellipticine via late-stage D-ring cyclization is described. Key features of the synthetic routes include trifluoroacetic acid-mediated formation of a lactone that is fused to a tetrahydrocarbazole derivative and its one-pot two-step ring opening and aromatization mediated by para-toluenesulfonic acid and palladium on carbon, respectively.

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.

A novel CAN-SiO2-mediated one-pot oxidation of 1-keto-1,2,3,4-tetrahydrocarbazoles to carbazoloquinones: Efficient syntheses of murrayaquinone A and koeniginequinone A

One-pot oxidations of substituted 1-keto-1,2,3,4-tetrahydrocarbazoles (1) to carbazole-1,4-quinones (2) are efficiently carried out by CAN-SiO 2-mediated reaction. This generalized protocol was successfully extended to the synthesis of two naturally occurring carbazoloquinones: murrayaquinone A (2b) and koeniginequinone A (2g). A plausible mechanism for this novel reaction involves formation of a 9-hydroxy-2,3,4,9-tetrahydro-1H- carbazole-1-one followed by rearrangement to 1-hydroxycarbazole derivatives, which are further oxidized by cerium (IV) to carbazoloquinones.

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.

A pentacyclic aurora kinase inhibitor (AKI-001) with high in vivo potency and oral bioavailability

Aurora kinase inhibitors have attracted a great deal of interest as a new class of antimitotic agents. We report a novel class of Aurora inhibitors based on a pentacyclic scaffold. A prototype pentacyclic inhibitor 32 (AKI-001) derived from two early lead

The reaction studies of α-chloroformylarylhydrazines with thiols, thioureas and α-cyclodiketones

The reactions of α-chloroformylarylhydrazines 1 with various types of mercaptan, thiourea and α-cyclodiketone have been studied intensively. 1-Arylhydrazinecarbothioates 2 were obtained via thioesterization when α-chloroformylarylhydrazines reacted with thiols. On the other hand, compounds 3 were obtained when α-chloroformylarylhydrazines reacted with thio-containing heterocyclic compounds, which suggested a totally different mechanism in these types of reactions. Further studies on the reaction of α-chloroformylarylhydrazines 1 with thiourea compounds confirmed a novel cyclization and de-cyclization mechanism, which led to give 2-arylhydrazinecarboximidamides 5 and 1,3,4-thiadiazolin-5-ones 6. In addition, various 1,3,4-oxadiazines 9 were obtained by reacting α-chloroformylarylhydrazines with α-cyclodiketones, showing ring cyclization was involved in this type of reaction.

Structure of Heptazoline

The details of the structure of heptazoline, a carbazole alkaloid from Clusena heptaphylla Wt. and Arn. have been reported.