6208-44-2

Usage

Chemical Class

Pyridoindole alkaloids

Structure

Tetrahydro derivative of 1H-pyrido[4,3-b]indole with a 2-phenylethyl moiety

Identification

Found in certain plant species

Pharmacological Activities

Anti-inflammatory, antioxidant, and anticancer properties

Biological Activity

Contributed by tetrahydro structure and phenylethyl group

Medicinal Applications

Potential use due to pharmacological activities and structural features

Upstream product

• 39742-60-4 1-(2-phenylethyl)-4-piperidinone 
• 108-42-9 3-chloro-aniline 
• 1346446-53-4 (3-chlorophenyl)-(1-phenethylpiperidin-4-ylidene)amine 

Downstream Products

• 62018-28-4 (4aS,9bR)-2-Phenethyl-2,3,4,4a,5,9b-hexahydro-1H-pyrido[4,3-b]indole 
• 62018-27-3 (4aα,9bα)-2,3,4,4a,5,9b-hexahydro-5-(1-oxopropyl)-2-(2-phenylethyl)-1H-pyrido<4,3-b>indole 

Relevant academic research and scientific papers

New route of benzyne cyclization for synthesis of 2,3,4,5-tetrahydro-1h-pyrido[4,3-b]indole derivatives avoiding highly toxic aryl hydrazines

A new route for the regioselective synthesis of 2,3,4,5-tetrahydro-1H-pyrido[4,3-b]indole derivatives was developed based on cyclization of 3-chlorophenylimine-N-alkyl-4-piperidones by "the complex bases" of NaNH2 or KNH2. The procedure was performed under variable reaction conditions in inert proton-free solvents, such as THF, dioxane, 1,2-dimethoxyethane, toluene, and xylene, at temperatures varying from 20C to boiling point of the solvent used. Toxic arylhydrazine intermediates occurring in the classical Fischer indole synthesis are avoided.

PROCESS FOR THE PREPARATION OF 2,3,4,5-TETRAHYDRO-1H-PYRIDO[4,3-B]INDOLE DERIVATIVES

The value of the invention is the application of the cyclization of Schiff-bases of the general formula (3a-i), where R1 - R8 are substituents defined in example 1, whereby R9 = Cl using complex bases of amides of group I of the periodic table (NaNH2, KNH2) from 2.1 - 5 equiv. and alcoholates of group I of the periodic table (t-BuONa, tBuOK) from 0.05 - 2 equiv. with the advantage of application of 3 equiv. of NaNH2 and 0.05 equiv. of t-BuONa, or their mixtures with PEG (m.w. = 500 - 6000), or crown ethers, or catalysts of phase transfer lithium in inert proton-free diluents, such as benzene, cyclohexane, toluene, xylene, 1,2-dimethoxyethane, dioxane, etc., with the advantage of using THF, at a temperature from 20 °C to boiling point of the diluent used, or with the application of organo-metallic bases such as LDA, t-BuLi in inert proton-free diluents at a temperature from -80°C to 25 °C.