6650-19-7

Upstream product

• 61-54-1 tryptamine 
• 104-87-0 4-methyl-benzaldehyde 
• 3380-71-0 1-(4-methylphenyl)-2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indole 
• 99-94-5 p-Toluic acid 

Relevant academic research and scientific papers

Selectivity-tunable oxidation of tetrahydro-β-carboline over an OMS-2 composite catalyst: preparation and catalytic performance

Controlling the reaction selectivity of organic transformations without losing high conversion is always a challenge in catalytic processes. In this work, a H3PO4·12WO3/OMS-2 nanocomposite catalyst ([PW]-OMS-2) was prepared through the oxidation of a Mn(ii) salt with sodium phosphotungstate by KMnO4. Comprehensive characterization indicates that different Mn2+precursors significantly affected the crystalline phase and morphology of the as-synthesized catalysts and only MnSO4·H2O as the precursor could lead to a cryptomelane phase. Moreover, [PW]-OMS-2 demonstrated excellent catalytic activity toward aerobic oxidative dehydrogenation of tetrahydro-β-carbolines due to mixed crystalline phases, enhanced surface areas, rich surface oxygen vacancies and labile lattice oxygen species. In particular, β-carbolines and 3,4-dihydro-β-carbolines could be obtained from tetrahydro-β-carbolines with very high selectivity (up to 99%) over [PW]-OMS-2viatuning the reaction solvent and temperature. Under the present catalytic system, scalable synthesis of a β-carboline was achieved and the composite catalyst showed good stability and recyclability. This work not only clarified the structure-activity relationship of the catalyst, but also provided a practical pathway to achieve flexible, controllable synthesis of functional N-heterocycles.

Mechanistic Studies on Bioinspired Aerobic C-H Oxidation of Amines with an ortho-Quinone Catalyst

We report herein our mechanistic studies of the ortho-quinone-catalyzed aerobic oxidation of primary, secondary, and tertiary amines. Two different catalytic pathways were discovered for the reductive half reactions: for primary amines, the reaction was found to proceed via a transamination pathway, while the reactions with secondary amines and tertiary amines proceeded via hydride transfer. We also found that the amine substrates could significantly promote the regeneration of the ortho-quinone catalyst in the oxidative half reaction, in which a proton transfer occurs between the amine substrates and catechol derivatives (the reduced form of the ortho-quinone catalyst).

Iodine-catalyzed chemoselective dehydrogenation and aromatization of tetrahydro-β-carbolines: A short synthesis of Kumujian-C, Eudistomin-U, Norharmane, Harmane Harmalan and Isoeudistomine-M

Temperature controlled chemoselective dehydrogenation and aromatization of tetrahydro-β-carbolines, using molecular I2 and H2O2, in DMSO solvent affords a practical access to a series of corresponding 3,4-dihydro-β-carbolines and β-carbolines respectively. This method has been successfully employed in the short synthesis of Kumujian-C, Eudistomin-U, Norharmane Harmane Harmalan and Isoeudistomin-M.

Cerium Chloride Catalyzed, 2-Iodoxybenzoic Acid Mediated Oxidative Dehydrogenation of Multiple Heterocycles at Room Temperature

Catalytic cerium chloride was found to activate 2-iodoxybenzoic acid (IBX) for the oxidative dehydrogenation of tetrahydroisoquinolines, tetrahydro-β-carbolines, and thiazolidines to their dehydrogenated and aromatic forms at room temperature in moderate to excellent yields. The robustness of the protocol was demonstrated by scaling up the reactions to multigram quantities.

N-Bromo-succinimide promoted synthesis of β-carbolines and 3,4-dihydro-β-carbolines from tetrahydro-β-carbolines

Herein, we report a facile synthesis of 3,4-dihydro-β-carbolines and aromatic β-carbolines from tetrahydro-β-carbolines, mediated by N-bromosuccinimide in toluene at 0°C to room temperature (rt), in good to moderate yields.

Synthetic study on the T3P-promoted one-pot preparation of 1-substituted-3,4-dihydro-β-carbolines by the reaction of tryptamine with carboxylic acids

A novel and efficient one-pot method has been developed for the synthesis of 1-substituted-3,4-dihydro-β-carbolines from tryptamine and a wide variety of carboxylic acids. The reaction was successfully applied to the synthesis of an important alkaloid har