512785-77-2

Upstream product

• 591-50-4 iodobenzene 
• 92136-39-5 N-tert-Butoxycarbonyl-1-amino-3-propyne 
• 98-80-6 phenylboronic acid 
• 24424-99-5 di-tert-butyl dicarbonate 
• 4530-20-5 BOC-glycine 
• 108-86-1 bromobenzene 

Downstream Products

• 512785-91-0 (R)-(E)-(1-benzylidene-2-hydroxy-3-methyl-butyl)-carbamic acid tert-butyl ester 
• 1020167-40-1 tert-butyl allyl(3-phenylprop-2-ynyl)carbamate 
• 1120371-15-4 (E)-{2-[hydroxy-(4-nitrophenyl)-methyl]-3-phenylallyl}-carbamic acid tert-butyl ester 
• 78168-74-8 3-phenyl-prop-2-ynylamine 
• 1333470-72-6 (5Z)-5-benzylidene-2-phenyl-4,5-dihydro-1,3-oxazole 
• 30011-36-0 3-phenylprop-2-yn-1-amine hydrochloride 

Relevant academic research and scientific papers

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.).

Dual use of propargylamine building blocks in the construction of polyheterocyclic scaffolds

The cyclization reactions of 2-(N-propargyl)imidazole-2-yl)indoles (synthesized via the hydroamination reaction between N-propargyl indole-2-carboxamides and propargylamine) have been investigated under Lewis acid- and base-promoted conditions. The polyhe

Graphitic Carbon Nitride Polymer as a Recyclable Photoredox Catalyst for Decarboxylative Alkynylation of Carboxylic Acids

Visible-light-induced heterogeneous photocatalysis for decarboxylative alkynylation has been performed. The using of cheap, metal-free and recyclable graphitic carbon nitride (g-C3N4) as the photoredox catalyst in the process enables

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

Structure activity relationship and modeling studies of inhibitors of lysine specific demethylase 1

Post-translational modifications of histone play important roles in gene transcription. Aberrant methylation of histone lysine sidechains have been often found in cancer. Lysine specific demethylase 1 (LSD1), which can demethylate histone H3 lysine 4 (H3K4) and other proteins, has recently been found to be a drug target for acute myeloid leukemia. To understand structure activity/selectivity relationships of LSD1 inhibitors, several series of cyclopropylamine and related compounds were synthesized and tested for their activities against LSD1 and related monoamine oxidase (MAO) A and B. Several cyclopropylamine containing compounds were found to be highly potent and selective inhibitors of LSD1. A novel series cyclopropylimine compounds also exhibited strong inhibitory activity against LSD1.Structure activity relationships (SAR) of these compounds are discussed. Docking studies were performed to provide possible binding models of a representative compound in LSD1 and MAO-A. Moreover, these modeling studies can rationalize the observed SARs and selectivity.

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.

Silver-Catalyzed Cyclization of Propargylic Amides to Oxazolines

A ligand-accelerated effect is observed in the cyclization of propargylic amides catalyzed by bis(pyridyl)silver(I) complexes, with an unexpected reversal of electronic demand to the analogous NH addition reaction. The catalyst was found to be effective for internal alkyne substrates, offering exclusive selectivity for the 5-exo-dig product. Differences in selectivity profile between gold- and silver-catalyzed processes are highlighted and discussed.

Decarboxylative Alkynylation and Carbonylative Alkynylation of Carboxylic Acids Enabled by Visible-Light Photoredox Catalysis

Visible-light-induced photocatalytic decarboxylative alkynylations of carboxylic acids have been developed for the first time. The reaction features extremely mild conditions, broad substrate scope, and avoids additional oxidants. Importantly, a decarboxy

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.

Highly efficient copper-catalyzed synthesis of internal alkynes via aerobic oxidative arylation of terminal alkynes

We have developed a novel and highly efficient, copper-catalyzed synthesis of internal alkynes via oxidative couplings of aromatic boronic acids with terminal alkynes at room temperature. The protocol uses inexpensive copper(I) oxide [Cu2O] as the catalyst, oxygen in the air as the stoichiometric oxidant; no ligand and sealed reaction vessels are required, and remarkable functional group tolerability is observed with coupling occurring.