58185-47-0

Upstream product

• 64-04-0 phenethylamine 
• 106-96-7 propargyl bromide 
• 141381-81-9 phenylethylamide of o-nitrophenylsulfonic acid 
• 122-78-1 phenylacetaldehyde 

Downstream Products

• 1177428-61-3 Se-phenyl N-(2-phenylethyl)-N-(prop-2-ynyl)carbamoselenoate 
• 1041425-06-2 N-phenylethyl-N-(2-propynyl)-2-chloroacetamide 

Relevant academic research and scientific papers

Non-Noble-Metal Metal-Organic-Framework-Catalyzed Carboxylative Cyclization of Propargylic Amines with Atmospheric Carbon Dioxide under Ambient Conditions

The coupling reaction of propargylic amines and carbon dioxide (CO2) to synthesize 2-oxazolidinones is an important reaction in industrial production, and yet harsh reaction conditions and noble-metal catalysts are often required to achieve high product yields. Herein, one novel noble-metal-free three-dimensional framework, [Mg3Cu2I2(IN)4(HCOO)2(DEF)4]n (1), assembled by magnesium and copper clusters was synthesized and applied to this reaction. Compound 1 displays excellent solvent stability. Importantly, 1, acting as heterogeneous catalyst, can highly catalyze the cyclization of propargylic amines with CO2 under atmospheric pressure at room temperature, which can be recycled at least five times without an obvious decrease of the catalytic activity. NMR spectroscopy, coupled with 13C-isotope- and deuterium-labeling experiments, clearly clarifies the mechanism of this catalytic system: CO2 was successfully captured and converted to the product of 2-oxazolidinones, the CC bond of propargylic amines can be effectively activated by 1, and proton transfer was involved in the reaction process. Density functional theory calculations are further conducted to uncover the reaction path and the crucial role of compound 1 during the reaction.

Access to Indole-Fused Benzannulated Medium-Sized Rings through a Gold(I)-Catalyzed Cascade Cyclization of Azido-Alkynes

Because benzannulated and indole-fused medium-sized rings are found in many bioactive compounds, combining these fragments might lead to unexplored areas of biologically relevant and uncovered chemical space. Herein is shown that α-imino gold carbene chem

Highly Efficient Conversion of Propargylic Amines and CO2 Catalyzed by Noble-Metal-Free [Zn116] Nanocages

The reaction of propargylic amines and CO2 can provide high-value-added chemical products. However, most of catalysts in such reactions employ noble metals to obtain high yield, and it is important to seek eco-friendly noble-metal-free MOFs catalysts. Here, a giant and lantern-like [Zn116] nanocage in zinc-tetrazole 3D framework [Zn22(Trz)8(OH)12(H2O)9?8 H2O]n Trz=(C4N12O)4? (1) was obtained and structurally characterized. It consists of six [Zn14O21] clusters and eight [Zn4O4] clusters. To our knowledge, this is the highest-nuclearity nanocages constructed by Zn-clusters as building blocks to date. Importantly, catalytic investigations reveal that 1 can efficiently catalyze the cycloaddition of propargylic amines with CO2, exclusively affording various 2-oxazolidinones under mild conditions. It is the first eco-friendly noble-metal-free MOFs catalyst for the cyclization of propargylic amines with CO2. DFT calculations uncover that ZnII ions can efficiently activate both C≡C bonds of propargylic amines and CO2 by coordination interaction. NMR and FTIR spectroscopy further prove that Zn-clusters play an important role in activating C≡C bonds of propargylic amines. Furthermore, the electronic properties of related reactants, intermediates and products can help to understand the basic reaction mechanism and crucial role of catalyst 1.

Efficient and Recyclable Cobalt(II)/Ionic Liquid Catalytic System for CO2 Conversion to Prepare 2-Oxazolinones at Atmospheric Pressure

Converting CO2 into value-added chemicals represents a promising way to alleviate the CO2 derived environmental issues, for which the development of catalysts with high efficiency and recyclability is very desirable. Herein, the catalytic system by combining cobalt source and ionic liquid (IL) has been developed as the efficacious and recyclable catalyst for the carboxylative cyclization of propargylic amine and CO2 to prepare 2-oxazolinones. In this protocol, various propargylic amines were successfully transformed into the corresponding 2-oxazolinones with CoBr2 and diethylimidazolium acetate ([EEIM][OAc]) as the catalyst under atmospheric CO2 pressure. It is worth noting that the turnover number (TON) of this transformation can be up to 1740, presumably being attributed to the cooperative effect of the cobalt and IL. Furthermore, the existence of IL enables the catalytic system to be easily recycled to 10 times without losing its activity.

One-pot preparation of pyrrole derivatives via the copper-catalyzed [4+1] annulation of propargylic amines with ethyl glyoxylate and phenylglyoxal in the presence of piperidine

We describe how copper(II) chloride efficiently catalyzes the [4+1] annulation of propargylamines with either ethyl glyoxylate or phenylglyoxal functioning as a C1 unit, in the presence of piperidine, which leads to a straightforward and one-pot preparati

Anti-methicillin resistant Staphylococcus aureus activity, synergism with oxacillin and molecular docking studies of metronidazole-triazole hybrids

MRSA causes 60-70% of Staphylococcus aureus infection in hospitals and it has developed resistance against the currently available drugs. Interestingly, a series of 35 metronidazole-triazole hybrids on screening against MRSA were found to be active. Compound 22 was found to be effective at 4 μg/mL concentration against nine strains of MRSA. The inhibitory activity was further enhanced upto 1 μg/mL when this compound was used in combination with oxacillin in 1:1 ratio. All the compounds were found to be non-toxic in THP-1 cell line upto a concentration of 50 μM. The time-kill kinetics studies suggested bacteriostatic nature of the compounds. In silico studies show that these compounds interact with Thr600, Ser598, Asn464, His583 and Tyr446 in the active site of PBP2a crystal structure from MRSA.

Palladium-catalyzed decarbonylative rearrangement of N-Allenyl seleno- and tellurocarbamates

Decarbonylative rearrangement of seleno- and tellurocarbamates carrying an allenyl group on the nitrogen was found to proceed in the presence of a palladium catalyst to afford 3-chalcogeno-1-azadienes. This transformation may involve oxidative addition of

Ln[N(SiMe3)2]3-Catalyzed Cross-Diinsertion of C≡N/C≡C into an N-H Bond: Facile Synthesis of 1,2,4-Trisubstituted Imidazoles from Propargylamines and Nitriles

A lanthanide-catalyzed sequential insertion of C≡N and C≡C into an N-H bond is presented. The convenient reaction, which proceeds under mild conditions, is an efficient method for preparing 1,2,4-trisubstituted imidazoles directly from readily available propargylamines and nitriles.

An expeditious and atom-economic synthesis of lead-like, medicinally important 4,5-dihydropyrazolo[1,5-a]pyrazin-6-ones

We have developed an expeditious and atom-economic synthesis of lead-like, privileged 4,5-dihydropyrazolo[1,5-a]pyrazin-6-ones, which is based on Sonogashira coupling and a two-step condensation with hydrazine hydrate leading to two ring-forming events, with full control over the two elements of diversity present.

Facile entry to 4,5,6,7-tetrahydro[1,2,3]triazolo[1,5-a]pyrazin-6-ones from amines and amino acids

A practical and high-yielding regioselective synthesis of several enantiopure 4,5,6,7-tetrahydro[1,2,3]triazolo[1,5-a]-pyrazin-6-ones is described starting from primary amines and α-amino acid derivatives in a three-step reaction sequence by employing a constrained intramolecular "click" reaction as the key step. The method obviates chromatographic purification of products. Wiley-VCH Verlag GmbH & Co. KGaA, 2008.