64252-02-4

Upstream product

• 487-89-8 Indole-3-carboxaldehyde 
• 79-24-3 Nitroethane 
• 83-34-1 3-Methylindole 

Downstream Products

• 299-26-3 1-(1H-indol-3-yl)propan-2-amine 
• 1292798-84-5 (R)-N-[1-(1H-indol-3-yl)propan-2-yl]-2-methoxyacetamide 
• 7795-51-9 (+)-alpha-Methyltryptamine 
• 4771-72-6 α-methyl-β-(3-indolyl)-1-nitroethane 

Relevant academic research and scientific papers

Guanidine-containing compound as well as preparation method and application thereof

The invention discloses a cyanoguanidine-containing compound as well as a preparation method and application thereof. The invention also discloses a composition containing the cyanoguanidine-structured compound (I) or a pharmaceutically acceptable salt thereof and a pharmaceutically acceptable carrier. The invention also discloses application thereof in preparation of analgesic drugs. The compounds of the invention are useful in the treatment of various pain.

Green synthesis of new pyrrolidine-fused spirooxindoles: Via three-component domino reaction in EtOH/H2O

An efficient, green and sustainable approach for the synthesis of novel polycyclic pyrrolidine-fused spirooxindole compounds was developed. The synthesis included a one-pot, three-component, domino reaction of (E)-3-(2-nitrovinyl)-indoles, isatins and chiral polycyclic α-amino acids under catalyst-free conditions at room temperature in EtOH-H2O. The salient features of this methodology are eco-friendliness, high yields and the ease of obtaining target compounds without the involvement of toxic solvents and column chromatography. These novel polycyclic pyrrolidine-fused spirooxindoles provide a collection of structurally diverse compounds that show promise for future bioassays and medical treatments.

INDOLE AHR INHIBITORS AND USES THEREOF

The present invention provides compounds useful as inhibitors of AHR, compositions thereof, and methods of using the same.

Synthesis of nitroalkenes involving a cooperative catalytic action of iron(III) and piperidine: A one-pot synthetic strategy to 3-alkylindoles, 2H-chromenes and N-arylpyrrole

An efficient and simple strategy has been developed to synthesize various substituted nitroalkenes involving a cooperative catalytic system of FeCl 3 and piperidine. This dual catalytic protocol simultaneously activates both electrophile and nucleophile and works under mild reaction conditions so that many sensitive functional groups were tolerated. Moreover, this cooperative catalytic reaction is also suitable for various one-pot reactions involving nitroalkenes such as, 2H-chromenes, N-arylpyrrole and Michael reaction with indole. Notably, this method is low-cost, efficient and environmentally friendly. Copyright

Ethylenediamine: A highly effective catalyst for one-pot synthesis of aryl nitroalkenes via henry reaction and dehydration

Ethylenediamine (H2NCH2CH2NH2) was found to be a highly effective catalyst for the condensation of aryl aldehydes with nitromethane (or nitroethane). When 1%-2% (mol%) of ethylenediamine was used as the catalyst, the one-pot reaction of aryl aldehydes with nitromethane (or nitroethane) by refluxing for 3-10 h efficiently afforded various arylnitroalkenes 1a-1y in 85%-97% yields. Ethylenediamine (H 2NCH2CH2NH2) was found to be a highly effective catalyst for the condensation of aryl aldehydes with nitromethane (or nitroethane). When 1-2 mol% of ethylenediamine was used as the catalyst, the one-pot reaction of aryl aldehydes with nitromethane (or nitroethane) by refluxing for 3-10 h efficiently afforded various aryl nitroalkenes 1a-1y in 85%-97% yields. Copyright

Straightforward preparation of biologically active 1-aryl- and 1-heteroarylpropan-2-amines in enantioenriched form

Because of the importance of developing stereoselective syntheses for single enantiomers, a selected panel of racemic biologically active 1-aryl- and 1-heteroarylpropan-2-amines has been prepared, followed by a study of their behavior in enzymatic kinetic resolution (KR) processes. For this purpose, lipase B from Candida antarctica (CAL-B) proved to be an ideal biocatalyst allowing the preparation of the corresponding enantioenriched (R)-amides and (S)-amines by aminolysis reactions. Likewise, dynamic kinetic resolutions (DKR) have been successfully achieved combining the use of CAL-B and Shvo's catalyst. This research constitutes the first example of a lipase-catalyzed DKR process of β-substituted isopropylamines.

An efficient synthesis of (E)-nitroalkenes catalyzed by recoverable diamino-functionalized mesostructured polymers

A clean, efficient, and simple method has been developed for synthesis of (E)-nitroalkenes using FDU-ED as an efficient catalyst. The reactions proceeded with moderate to high yields (60-96%) under mild conditions. The catalyst FDU-ED is recyclable and can be reused more than seven times without significant loss of activity and selectivity.

Synthesis of deuterium labeled tryptamine derivatives

The synthesis of deuterium labeled tryptamine derivatives, [2-(1H-indol-3-yl)-[2H4]-ethyl]-dimethylamine (DMT), [2H10]-diethyl-[2-(1H-indol-3-yl)-ethyl]-amine (DET), [2-(1H-indol-3-yl)-ethyl]-[2H6]-dipropyl-amine (DPT) and [2H2]-alpha-methyltryptamine (AMT) is described. The isotopically labeled compounds are used as internal standards in gas chromatography-mass spectrometry (GC-MS) assays.

Synthesis of Carbazoles via Diels-Alder Reaction of 3-Vinylindoles

Diels-Alder reaction of 3-(β-nitrovinyl)indole (1) with acrylonitrile, ethyl acrylate and cinnamaldehyde gives the carbazoles 4, 5 and 6 respectively by the loss of nitro group and aromatization.The reaction of 3-(β-nitro-β-methylvinyl)indole (2) with acrylonitrile and ethyl acrylate gives the carbazoles 7 and 8 respectively.Diels-Alder reaction of 3-(β-carbethoxyvinyl)indole (3) with acrylonitrile and ethyl acrylate gives the tetrahydrocarbazoles 10 and 12 (at lower temperature) and carbazoles 9 and 11 (at higher temperature), respectively.