23504-14-5

Upstream product

• 106-96-7 propargyl bromide 
• 95-55-6 2-amino-phenol 
• 1216-96-2 2-aminophenyl p-toluenesulfonate 
• 326598-28-1 2-(N-prop-2'-ynylamino)phenyl p-toluenesulfonate 

Downstream Products

• 148-24-3 8-quinolinol 
• 343270-95-1 2-methylidene-3,4-dihydro-2H-1,4-benzoxazine 
• 73222-95-4 N-(2-hydroxyphenyl)-N-(prop-2-yn-1-yl)benzamide 
• 73222-93-2 N-(2-hydroxyphenyl)-N-(prop-2-yn-1-yl)acetamide 
• 1287759-54-9 N-(2-hydroxyphenyl)-4-methyl-N-(prop-2-yn-1-yl)benzene sulfonamide 
• 1571119-54-4 methyl 2-(4-{[(2-hydroxyphenyl)amino]methyl}-1H-1,2,3-triazol-1-yl)acetate 

Relevant academic research and scientific papers

Design, synthesis and antibacterial evaluation of novel 1,2,3-triazole derivatives incorporating 3′-deoxythymidine

A series of novel 1,2,3-triazole derivatives incorporating 3′-deoxythymidine were designed, synthesised and characterised. Antibacterial activity against Escherichia coli and Staphylococcus aureus was evaluated for all of the synthesised compounds and com

Copper(II)-Catalyzed [4+1] annulation of propargylamines with N,O-acetals: Entry to the synthesis of polysubstituted pyrrole derivatives

Described herein is the CuCl2-catalyzed [4+1] annulation of a variety of propargylamines with N,O-acetals that function as a C1 unit, leading to the production of polysubstituted pyrrole derivatives. Three important features of the N,O-acetal during the [4+1] annulation series via 5-endo-dig cyclization are described: an enolizable substituent adjacent to the central sp3-carbon is required, the central sp3-carbon displays the functions of both an electrophile and a nucleophile, and liberation of the secondary amine smoothly leads to the aromatization. A CuCl2-catalyzed [4+1] annulation of propargylamines with N,O-acetals having an ester, a ketone, and an amide moiety, leading to the facile preparation of polysubstituted pyrrole derivatives is presented. This annulation series was achieved through 5-endo-dig cyclization and subsequent aromatization in one pot.

Synthesis and preliminary biological evaluation of the first 99mTc(I)-specific semi-rigid tridentate ligand based on a click chemistry strategy

A novel bifunctional chelating agent based on a click chemistry strategy has been synthesized and characterized on the basis of spectroscopic techniques. The metal chelating part of this new class of tridentate N2O ligand combined a triazole un

An alternative synthesis of 2-alkylidene-3,4-dihydro-2 H-1,4-benzoxazines by intramolecular gold-catalyzed hydroalkoxylation of 2-(prop-2-yn-1-ylamino) phenols

An efficient gold-catalyzed procedure to synthesize 2-alkylidene-3,4- dihydro-2H-1,4-benzoxazines has been developed starting from 2-alkynyl-substituted phenols. This is an intramolecular hydroalkoxylation reaction on alkynes tethered to a phenol moiety that represents a valuable alternative to the already reported transition-metal-catalyzed procedures. Georg Thieme Verlag Stuttgart · New York.

Palladium-catalyzed heteroannulation leading to heterocyclic structures with two heteroatoms: A highly regio- and stereoselective synthesis of (Z)-4-alkyl-2-alkyl(aryl)idene-3,4-dihydro-2H-1,4,-benzoxazines and (Z)-3-alkyl(aryl)idene-4-tosyl-3,4-dihydro-2H-1,4-benzoxazines

A highly convenient method has been developed for the synthesis of (Z)-4-alkyl-2-alkyl(aryl)idene-3,4-dihydro-2H-1,4-benzoxazines 9 and (Z)-3-alkyl(aryl)idene-4-tosyl-3,4-dihydro-2H-1,4-benzoxazines 34-38 through palladium - copper-catalyzed reactions. Aryl halides 7 reacted with 2-[Nalkyl(benzyl)-N-prop-2′-ynyl]aminophenyl tosylate 6 in the presence of (PPh3)2PdCl2 (3 mol %), CuI(5 mol %) in triethylamine at room temperature to yield 2-[N-alkyl(benzyl)-N-(3-aryl-prop-2′-ynyl)]aminophenyl tosylates 8 in extremely good yields (72-96%). The latter could then be cyclized with KOH in ethanol - water to Z-9 in a highly regio- and stereoselective manner. Similarly, palladium copper-catalyzed reaction of 2-(prop-2′-ynyloxy)aniline (21) with aryl iodides 7 led to 22-26 which after tosylation and cyclization with cuprous iodide in CH3CN in the presence of K2CO3 and Bu4-NBr led to the (Z)-3-alkyl(aryl)idene-4-tosyl 3,4-dihydro-2H-1,4-benzoxazines 34-38 in good overall yields. The Z-stereochemistry of the products was established from 1H NMR spectra, 3JCH values (between vinylic proton and methylenic carbon of the heterocyclic ring), NOE experiments, and X-ray analysis· The method was also found to be suitable for the synthesis of bis(benzoxazinylated) derivatives 17, 39, and 2-alkyl-3,4-dihydro-2H-1,4-benzoxazines 18. Our method for the synthesis of 3,4-dihydro-2H-1,4-benzoxazines is highly efficacious, using easily available starting materials under very mild conditions. Also the synthesis of some novel 5-substituted uracil derivatives 40 and 41 containing the benzoxazinyl moiety and of potential biological interest is being reported.