22774-68-1

Upstream product

• 106-96-7 propargyl bromide 
• 99-09-2 3-nitro-aniline 
• 13331-27-6 m-nitrobenzene boronic acid 
• 624-65-7 2-propynyl chloride 
• 6165-75-9 propargyl benzenesulfonate 

Downstream Products

• 607-34-1 5-nitroquinoline 
• 1616405-31-2 N-methyl-3-nitro-N-((1-tosyl-1H-1,2,3-triazol-4-yl)methyl)aniline 
• 1616405-41-4 (E)-4-methyl-N-((1-methyl-6-nitro-1H-indol-3-yl)methylene)benzenesulfonamide 
• 1616405-63-0 N-methyl-3-nitro-N-(prop-2-yn-1-yl)aniline 
• 1234345-28-8 C₁₆H₂₄N₅O₆P 
• 1092371-33-9 5-(4-hydroxy-3,5-dimethoxy-phenyl)-9-{4-[(3-nitro-phenylamino)-methyl]-[1,2,3]triazol-1-yl}-5,8,8a,9-tetrahydro-5aH-furo[3',4':6,7]naphtho[2,3-d][1,3]dioxol-6-one 

Relevant academic research and scientific papers

Alkynation of chlorinated cotarnine by silver propargylamines

Chlorinated cotarnine was alkynated in the 1-position upon brief heating in acetonitrile with silver acetylenides of propargylamines to form the corresponding propargylamine derivatives.

Synthesis and biological evaluation of coumarin-linked 4-anilinomethyl-1,2,3-triazoles as potent inhibitors of carbonic anhydrases ix and xiii involved in tumorigenesis

A series of coumarin-linked 4-anilinomethyl-1,2,3-triazoles (6a–t) was synthesized via a molecular hybridization approach, through carbon C-6 of the coumarin moiety. The synthesized compounds were evaluated for their inhibition of carbonic anhydrase (CA)

Synthesis and Photophysical Characterization of 2,3-Dihydroquinolin-4-imines: New Fluorophores with Color-Tailored Emission

In this study, a series of variously substituted 2,3-dihydroquinolin-4-imines (DQIs) were synthesized from N-substituted propargylanilines by copper(I)-catalyzed annulation. The approach adopted in this study under mild, effective conditions exhibited broad substrate tolerance, particularly for functional groups substituted on anilines. Most of the DQI derivatives synthesized under optimal conditions were obtained in good isolated yields of 63–88 %. 2,3-Dihydroquinolinimine thus obtained was easily converted to important structures like 2,3-dihydroquinolone and tetrahydrobenzodiazepin-5-one, confirming the importance of this strategy in constructing various heterocycles. Surprisingly, 2,3-dihydroquinolinimines thus obtained exhibited bright fluorescence with quantum yields up to 66 %. The density functional theory (DFT) and time-dependent DFT (TD-DFT) calculations were performed for understanding the excited-state nature of DQI system. Accordingly, a tailored DQI derivative bearing methoxy group at C-6 position and acetoxy group at C-7 position was designed and synthesized to give emission at 559 nm with redshift compared to the 7-methoxy substituted DQI. A detailed study of DQI structures with their photophysical properties was performed with five control molecules and consequently demonstrated the uniqueness of the chemical structures of DQIs.

Stereospecific Ring Opening and Cycloisomerization of Aziridines with Propargylamines: Synthesis of Functionalized Piperazines and Tetrahydropyrazines

Stereospecific Cu-catalyzed nucleophilic ring opening of N-sulfonylaziridines with propargylamines and subsequent hydroamination afford piperazines, which leads to double-bond isomerization to furnish tetrahydropyrazines. Optically active aziridines can be cross-coupled with high enantiomeric purities (>98% ee).

Efficient synthesis of new antiproliferative steroidal hybrids using the molecular hybridization approach

A series of steroidal hybrids with different terminal bioactive scaffolds were synthesized using the molecular hybridization approach and further evaluated for their antiproliferative activity against several cancer cell lines of different origins using t

Synthesis of substituted 3-indolylimines and indole-3-carboxaldehydes by rhodium(II)-catalyzed annulation

An efficient Cu/Rh-catalyzed method is proposed for the synthesis of 3-indolylimines from N-propargylanilines through Rh(II)-catalyzed denitrogenative annulation of N-sulfonyl-1,2,3-triazoles. Further combined with hydrolysis or reduction, a one-pot method is developed to enable the direct incorporation of an imine, aldehyde, or amine group into an indole system from an alkyne. A variety of substituted 3-indolylimines, indole-3-carboxaldehydes, and 3-Indolylmethanamines are synthesized in good yields.

One-pot synthesis of N-aryl propargylamine from aromatic boronic acid, aqueous ammonia, and propargyl bromide under microwave-assisted conditions

A facile, one-pot synthesis of N-aryl propargylamine from aromatic boronic acid, aqueous ammonia, and propargyl bromide has been achieved under microwave-assisted conditions. The reactions can be smoothly completed within a total 10 min through a two-step procedure, including copper-catalyzed coupling of aromatic boronic acids with aqueous ammonia and following propargylation by propargyl bromide.

A microwave-assisted three-component synthesis of arylaminomethyl ?acetylenes: A facile access to terminal alkynes

A simple, rapid, one-pot synthesis of arylaminomethyl acetylenes is achieved under microwave-assisted conditions (power? =? 5 W) using aromatic boronic acids, aqueous ammonia, propargyl halides, copper(I) oxide and water as the solvent. The reactions are complete within ten minutes affording good to excellent yields of the products. Georg Thieme Verlag Stuttgart. New York.

INFLUENCE OF THE NATURE OF THE LEAVING GROUP ON THE RATES OF THE REACTIONS OF ALKYNYL HALIDES AND ALKYNYL SULFONATES WITH PRIMARY ARYLAMINES IN ACETONITRILE

For aminolysis reactions we have determined and quantitatively asessed the nonadditivity of the joint influence of the electronic effects of the substituents and the nature of the leaving group in alkynyl halide-alkynyl sulfonate-arylamine systems.