16017-26-8

Upstream product

• 124316-00-3 1-<<(Triphenylphosphoranylidene)amino>methyl>benzotriazole 
• 766-97-2 4-n-methylphenylacetylene 
• 106-38-7 para-bromotoluene 
• 2450-71-7 Propargylamine 
• 1600515-03-4 tert-butyl 3-p-tolylprop-2-ynylcarbamate 
• 624-31-7 4-tolyl iodide 
• 16017-24-6 3-p-tolylprop-2-yn-1-ol 
• 1453164-22-1 1-(3-azidoprop-1-yn-1-yl)-4-methylbenzene 

Downstream Products

• 76304-54-6 3-(4-methylphenyl)pyrrole 
• 51382-65-1 3-Methyl-4-p-tolyl-5H-furan-2-one 
• 486435-28-3 N-[3-(4-methylphenyl)-prop-2-ynyl]-4-(4'-trifluoromethyl-biphenyl-2-carbonylamino)-1-methyl-pyrrole-2-carboxylic acid amide 
• 389602-03-3 N-[3-(4-methylphenyl)-prop-2-ynyl]-3-(4'-trifluoromethyl-biphenyl-2-carbonylamino)-benzoic acid amide 
• 1228797-81-6 2-[3-(4-methylphenyl)-2-propynylamino]-1,4-naphthoquinone 
• 1313367-77-9 C₂₅H₂₅N₃ 
• 1313367-74-6 C₁₇H₂₅N₃ 
• 1315356-51-4 methyl 4-(p-tolyl)-4a,5,6,7-tetrahydro-2H-cyclopenta[b]pyridine-4a-carboxylate 
• 1315356-41-2 ethyl 4-(p-tolyl)-2,4a,5,6,7,8-hexahydroquinoline-4a-carboxylate 
• 1513574-77-0 1,5-dihydro-4-hydroxy-3-(4-methylphenyl)-2H-pyrrol-2-one 
• 1600515-03-4 tert-butyl 3-p-tolylprop-2-ynylcarbamate 

Relevant academic research and scientific papers

Benzene-1,3,5-triyl Triformate (TFBen)-Promoted Palladium-Catalyzed Carbonylative Synthesis of 2-Oxo-2,5-dihydropyrroles from Propargyl Amines

In this letter, we developed a palladium-catalyzed procedure for the cyclocarbonylation of propargyl amines. Benzene-1,3,5-triyl triformate (TFBen) has been explored as the CO source and also as the key promotor. Various substituted 2-oxo-dihydropyrroles were produced in a facile manner in good yields (up to 90%).

Synthesis of 3-Keto Pyridines from the Conjugated Allenone – Alkynylamine Oxidative Cyclization Catalyzed by Supported Au Nanoparticles

Recyclable supported Au nanoparticles on TiO2 catalyze the cyclization of N-propargyl or N-homopropargyl β-enaminones followed by dehydrogenation (aromatization) leading to substituted 3-keto pyridines or 4-picolines in very good yields. This pathway is in contrast to their known cyclization in the presence of Au(I) or Au(III) catalysts which provides 1,4-oxazepines, instead. The enaminones are formed in situ upon mixing a conjugated allenone or allenyl ester with the alkynylamine, thus the pyridine-forming transformation is typically a one pot process. (Figure presented.).

Development of a telescoped flow process for the safe and effective generation of propargylic amines

Propargylic amines are important multifunctional building blocks that are frequently exploited in the synthesis of privileged heterocyclic entities. Herein we report on a novel flow process that achieves the safe and effective on-demand synthesis of propargylic amines in a telescoped manner. This process minimizes exposure to hazardous azide intermediates and renders a streamlined route into these building blocks. The value of this approach is demonstrated by the rapid generation of a small selection of drug-like thiazolines that result from a high-yielding reaction cascade between propargylic amines with different aryl isothiocyanates.

One-Pot Copper-Catalyzed Cascade Bicyclization Strategy for Synthesis of 2-(1H-Indol-1-yl)-4,5-dihydrothiazoles and 2-(1H-Indol-1-yl)thiazol-5-yl Aryl Ketones with Molecular Oxygen as an Oxygen Source

An atom-economical method for synthesizing N-heterocyclic indoles from readily available o-alkynylphenyl isothiocyanates and propargylamine derivatives is reported. This method involves a copper-catalyzed cascade bicyclization process consisting of an int

Ag NPs decorated on a COF in the presence of DBU as an efficient catalytic system for the synthesis of tetramic acids via CO2 fixation into propargylic amines at atmospheric pressure

CO2 fixation reactions by inserting it in reactive organic compounds are very challenging for the utilization of this abundant and harmful gas present in air and thus to mitigate this greenhouse gas responsible for global warming. This can be achieved by appropriate design of functionalized porous nanocatalysts having high surface areas and porosity and good CO2 uptake capacity. Herein, we first report the decoration of silver nanoparticles (NPs) over the surface of a covalent organic framework (COF) material TpPa-1 synthesized through the polycondensation of 2,4,6-triformylphloroglucinol (TFP) and p-phenylenediamine. The resulting material Ag@TpPa-1 was thoroughly characterized by N2 adsorption/desorption, powder X-ray diffraction (PXRD), FE-SEM, TEM, UV-Vis, FT IR and thermogravimetric techniques. This Ag NP decorated porous COF in the presence of DBU exhibited excellent catalytic activity for the synthesis of tetramic acids from a variety of propargylic amine derivatives at 60 °C under atmospheric pressure of carbon dioxide via formation of oxazolidinones, where CO2 acts as a C1 reagent. The Ag@TpPa-1 catalyst exhibited excellent recycling efficiency for the synthesis of tetramic acid with no leaching of Ag from the catalyst surface.

Differentiating alkyne reactivity in the post-Ugi transformations: Access to polycyclic indole-fused frameworks

The Ugi adducts prepared from propiolic acids, propargylamines, indole-2-carbaldehydes, and isocyanides were utilized to assemble polycyclic indole-fused frameworks via two consecutive carbocyclizations involving triple bonds. First, the peptidyl position

Domino Aza-Michael-ih-Diels-Alder Reaction to Various 3-Vinyl-1,2,4-triazines: Access to Polysubstituted Tetrahydro-1,6-naphthyridines

A straightforward domino aza-Michael-inverse-electron-demand-hetero-Diels-Alder/retro-Diels-Alder reaction between primary and secondary propargylamine derivatives and 3-vinyl-1,2,4-triazines is developed highlighting not only the uniqueness of this dual-

Electrophile-Mediated Reactions of Functionalized Propargylic Substrates

Metal-free halogen, chalcogen, or oxocarbenium ion mediated yne-carbonyl or yne-thioxo transformations of a range of N- and O-propargylic compounds have been studied. This investigation has led to the development of a mild, economic, and effective method for the synthesis of functionalized 4H-1,3-oxazines, 4H-1,3-thiazines, 4,5-dihydrothiazoles, and α-substituted enones. The structure of the propargylic substrate and the nature of electrophile influence both the outcome and regioselectivity of processes. Metal-free electrophile-mediated transformations of various N- and O-propargylic compounds have been studied. The scope and limitations of these reactions have been evaluated by using a broad range of substrates.

Novel method of tetramic acid synthesis: Silver-catalyzed carbon dioxide incorporation into propargylic amine and intramolecular rearrangement

Tetramic acid derivatives have been studied as biologically active heterocycle structures for pharmaceutical or agricultural chemicals. Conventional preparative approaches often require highly functionalized starting materials and harsh heating conditions in basic media. The present report provides a conceptually new synthetic strategy for the synthesis of tetramic acid derivatives from easily available propargylic amines and carbon dioxide with a silver salt and DBU under mild reaction conditions.

Alkynylation of aryl bromides with propargylamines catalyzed by a palladium-tetraphosphine complex

The tetraphosphine all-cis-1,2,3,4-tetrakis(diphenylphosphinomethyl) cyclopentane in combination with [Pd(C3H5)Cl]2 affords a very efficient catalyst for the alkynylation of aryl bromides with propargylamines. Higher reactions rates were observed with N,N- dialkylpropargylamines than with N-methylpropargylamine or propargy lamine. A wide variety of substituents such as alkyl, phenyl, methoxy, dimethylamino, fluoro, trifluoromethyl, acetyl, benzoyl, formyl, carboxylate, nitro, or nitrile, on the aryl bromides are tolerated. High turnover numbers can be obtained with most of these aryl bromides. The coupling reaction of sterically very congested aryl bromides such as 9-bromoanthracene or 2,4,6- triisopropylbromobenzene also proceeds in good yields. Georg Thieme Verlag Stuttgart.