1353013-66-7

Upstream product

• 872-32-2 2-methyl-1H-pyrroline 
• 81120-68-5 5-methyl-1-(toluene-4-sulfonyl)-2,3-dihydro-1H-pyrrole 
• 98-59-9 p-toluenesulfonyl chloride 
• 5891-21-4 5-chloro-2-pentanone 
• 95-20-5 2-methyl-1H-indole 
• 3634-89-7 N-(p-toluenesulfonyl)aziridine 
• 100-63-0 phenylhydrazine 
• 2731-06-8 2-methyltryptamine 
• 58754-95-3 N-(2,2-dimethoxyethyl)-p-toluenesulfonamide 

Downstream Products

• 1616347-85-3 2-methyl-2'-methylene-1'-tosylspiro[indole-3,4'-piperidine] 

Relevant academic research and scientific papers

Exploiting the σ-phylic properties of cationic gold(i) catalysts in the ring opening reactions of aziridines with indoles

A study on the SN2-type ring opening reactions of aziridines with indoles as nucleophiles is reported. Under gold(i) catalysis a great variety of tryptamine derivatives were prepared in good to excellent yields with complete stereocontrol when chiral aziridines were used. We demonstrated that cationic gold(i) catalysts are superior Lewis acids to the previously reported group 3, 12 and 13 metals in terms of catalyst loading and reaction yields. Moreover, complete regioselectivity was observed for 2-phenyl-N-tosylaziridine; whereas, regioselectivity up to 10:1 ratio was observed with 2-methyl-N-tosylaziridine. Finally, a preliminary study on the dearomatization reactions giving rise to pyrroloindolines is also reported.

Synthesis of Carbolines via Palladium/Carboxylic Acid Joint Catalysis

The combination of a Pd(0) complex with benzoic acid converts propargylic tryptamines to the corresponding tetrahydro-β-carbolines. The method uses unprotected indoles and affords the desired products with ample functional group tolerance. Detailed modeling studies reveal a close synergy between the organic and metal catalysts, which enables sequential alkyne isomerization, indole C-H activation, and eventual C-C reductive elimination to afford the target heterocycles.

Gold-Catalyzed Intramolecular Tandem Cyclization of Indole-Ynamides: Diastereoselective Synthesis of Spirocyclic Pyrrolidinoindolines

A gold-catalyzed intramolecular tandem cyclization of indole-ynamide affords tetracyclic spirocyclic pyrrolidinoindoline bearing an all-carbon quaternary stereocentre in a single step; however, when the reaction was carried out in the presence of BF3·Et2O, the corresponding tricyclic spirocyclic pyrrolidinoindoline-based enones are produced through a key 1,5-hydride shift. The developed chemistry provides a diastereoselective and straightforward entry to structurally diverse polycylic pyrrolidinoindolines from indole-ynamides in one-pot reactions under mild conditions.

Rapid access to spirocyclized indolenines via palladium-catalyzed cascade reactions of tryptamine derivatives and propargyl carbonate

We report the intermolecular palladium-catalyzed reaction of tert-butyl propargyl carbonate with tryptamine derivatives or other indole-containing bis-nucleophiles. The reaction proceeds under mild conditions and with low catalyst loadings to afford novel spiroindolenine products in good to high yields.

Rhodium(I)-catalyzed cycloisomerization of nitrogen-tethered indoles and alkylidenecyclopropanes: Convenient access to polycyclic indole derivatives

At the end of its tether: A new synthetic protocol for the preparation of polycyclic indole derivatives has been developed from a rhodium(I)-catalyzed cycloisomerization of a nitrogen-tethered indole and alkylidenecyclopropane, affording the corresponding

Synthesis of tryptamine derivatives via a direct, one-pot reductive alkylation of indoles

An efficient, one-pot reductive alkylation of indoles with N-protected aminoethyl acetals in the presence of TES/TFA is reported. It represents the first general method for the direct synthesis of tryptamine derivatives from indoles and nitrogen-functionalized acetals. This convergent and versatile approach employs safe and inexpensive reagents, proceeds under mild conditions, and tolerates several functional groups. The new procedure was efficiently applied to a gram-scale synthesis of both luzindole, a reference MT2-selective melatonin receptor antagonist, and melatonin.

A one-pot three-component reaction for the preparation of highly functionalized tryptamines

We have developed a general one-pot method to provide highly functionalized tryptamine derivatives, via a Fischer indole type pathway. In this article, we demonstrate optimal conditions for a one-pot indole synthesis, allowing for the synthesis of a broad scope of 2-methyl tryptamine derivatives and a precursor for the synthesis of the core structure of some akuammiline alkaloids. Additionally, further modification of the indole products is described.