54268-27-8

Upstream product

• 61-49-4 [2-(1H-indol-3-yl)-ethyl]-methylamine 
• 201230-82-2 carbon monoxide 
• 120-72-9 indole 
• 72773-04-7 N-formylbenzotriazole 
• 67909-99-3 ethyl 2-(1H-indole-3-yl)ethylcarbamate 
• 6502-82-5 N_b-formyltryptamine 
• 61-54-1 tryptamine 
• 2258-42-6 formyl acetic anhydride 
• 64-18-6 formic acid 

Downstream Products

• 61-50-7 N,N-dimethyltryptamine 
• 474657-72-2 Desformylflustrabromine 

Relevant academic research and scientific papers

Marine Alkaloids. Part 4. A Formamide, Flustrabromine, from the Marine Bryozoan Flustra foliacea

The isolation and structure elucidation of a marine alkaloid from the bryozoan Flustra foliacea is described.The alkaloid, 6-bromo-2-(1,1-dimethylallyl)-Nb-formyl-Nb-methyltryptamine (1), has been shown to consist of two rotameric forms reflecting hindered rotation around carbon-nitrogen bond of the formamide function.Furthermore, each rotamer exists in equilibrium with an intramolecularly associated form where the amide nitrogen is associated with the aromatic system.

Photoinduced oxygenation of tryptamines by aromatic amine N-oxides

Irradiation (1) (253-7 nm) of Na,Nb-dimethyltryptaimne with pyridine N-oxide or benzo[c]cinnoline N-oxide in CH2Cl2 yielded 1,8-dimethyl-3a-hydroxy-1,2,3,3a,8-8a,- hexahydropyrrolo[2,3-b]indole (19), while with visible light Nb-(4-cyanobutadienyl)-Na,Nb,- dimethyltryptamine (21) was obtained. This method was applied to trimethyltryptamine and the corresponding oxindole (34) and the N-formyl derivative (20) were obtained.

Sequential One-Pot Vilsmeier-Haack and Organocatalyzed Mannich Cyclizations to Functionalized Benzoindolizidines and Benzoquinolizidines

The development of new one-pot sequential cyclizations involving a Vilsmeier-Haack reaction followed by an organocatalyzed Mannich reaction is reported. This synthetic strategy gives access to functionalized indolizidines and quinolizidines in one operation from readily synthesized precursors. Yields and diastereoselectivities are good to excellent when formamides are used to trigger the key step, bearing either an electron-rich aryl or a pyrrole as the nucleophilic partner in the first cyclization.

Pd/Cu Cocatalyzed Oxidative Tandem C-H Aminocarbonylation and Dehydrogenation of Tryptamines: Synthesis of Carbolinones

The Pd/Cu cocatalyzed oxidative tandem C-H aminocarbonylation and dehydrogenation was developed, affording carbolinones with molecular oxygen as the terminal oxidant. Natural product strychnocarpine and its derivatives were prepared conveniently using this strategy.

Total synthesis of flustramine C via dimethylallyl rearrangement

(Chemical Equation Presented) The marine natural product flustramine C from the bryozoan Flustra foliacea was synthesized in five steps and 38% yield starting from Nb-methyltryptamine. The key step is the biomimetic oxidation of the natural pro

Indole derivatives with antimycobacterial activity

1,3-Dinitro-2-(indol-3'-yl)-propanes 3 are synthesized by Michael reaction of nitromethane with the indolylnitroethenes 2. - Reaction of the aldehydes 4 and 10 with the benzylamines 12 as well as the reaction of the indolylalkylamines 6a and 9a with the benzaldehydes 11 lead to Schiff bases which are reduced to N-benzyl-(indol-3-ylmethyl)-amines 13 and N-benzyl-(indol-3-ylethyl)-amines 14, respectively; tert amines 16 are synthesized via the formamides 15, amines 18 are prepared according to Mannich. - Inhibitory effects on Mycobacterium tuberculosis H 37 Ra are investigated, a structure-activity relationship is discussed.