79568-30-2

Upstream product

• 53244-68-1 2-(methylthio)-4,4-dimethyl-4,5-dihydro-1,3-oxazole 
• 4294-57-9 para-methylphenylmagnesium bromide 
• 30093-99-3 4,4-dimethyl-2-oxazoline 
• 106-38-7 para-bromotoluene 
• 874-60-2 4-methyl-benzoyl chloride 
• 124-68-5 2-Amino-2-methyl-1-propanol 
• 104-85-8 para-methylbenzonitrile 
• 99-94-5 p-Toluic acid 
• 59046-28-5 p-toluoyl-1H-1,2,3-benzotriazole 
• 106-43-4 para-chlorotoluene 
• 104-87-0 4-methyl-benzaldehyde 
• 36719-51-4 3,3-diethyl-1-(4-methylphenyl)-1-triazene 
• 106-49-0 p-toluidine 

Downstream Products

• 186962-73-2 4,4-Dimethyl-2-(4-pentyl-phenyl)-4,5-dihydro-oxazole 
• 186962-76-5 2-bromo-4-n-pentylbenzyl alcohol 
• 186962-78-7 2-bromo-4-n-pentylbenzyl chloride 
• 186962-77-6 2-bromo-4-n-pentylbenzaldehyde 
• 186962-74-3 2-bromo-4-n-pentylbenzoic acid 
• 186962-75-4 2-(2-Bromo-4-pentyl-phenyl)-4,4-dimethyl-4,5-dihydro-oxazole 
• 1386451-16-6 4,4-dimethyl-2-{4-methyl-2-[bis(trimethylsiloxy)(methyl)silyl]phenyl}-4,5-dihydrooxazole 
• 1422466-78-1 4,4-dimethyl-2-(4-tridecylphenyl)-4,5-dihydrooxazole 
• 1422466-76-9 4-vinylbenzyl 4-(5-(4-tridecylphenyl)-1,3,4-oxadiazol-2-yl)benzoate 
• 1422466-82-7 4-tridecylbenzohydrazide 
• 1422466-83-8 2-dodecyl-4-tridecylbenzohydrazide 
• 1422466-84-9 4-tridecylbenzoyl chloride 
• 1422466-85-0 2-dodecyl-4-tridecylbenzoyl chloride 
• 1422466-86-1 methyl 4-(2-(4-tridecylbenzoyl)hydrazinecarbonyl)benzoate 

Relevant academic research and scientific papers

Clickable azide-functionalized bromoarylaldehydes – synthesis and photophysical characterization

Herein, we present a facile synthesis of three azide-functionalized fluorophores and their covalent attachment as triazoles in Huisgen-type cycloadditions with model alkynes. Besides two ortho- and para-bromo-substituted benzaldehydes, the azide functionalization of a fluorene-based structure will be presented. The copper(I)-catalyzed azide–alkyne cycloaddition (CuAAC) of the so-synthesized azide-functionalized bromocarbaldehydes with terminal alkynes, exhibiting different degrees of steric demand, was performed in high efficiency. Finally, we investigated the photophysical properties of the azide-functionalized arenes and their covalently linked triazole derivatives to gain deeper insight towards the effect of these covalent linkers on the emission behavior.

Aerobic C(sp2)-H Hydroxylations of 2-Aryloxazolines: Fast Access to Excited-State Intramolecular Proton Transfer (ESIPT)-Based Luminophores

The direct hydroxylation of 2-aryloxazolines via a deprotonative magnesiation using TMPMgCl·LiCl and subsequent oxidation with molecular oxygen or air as a green oxidant is reported. This method proceeds under mild conditions at room temperature with high regioselectivity and chemoselectivity. The obtained phenols exhibit tunable luminescence properties, induced by excited-state intramolecular proton transfer. This method opens a new opportunity for the sustainable synthesis of luminescent organic molecules.

Palladium-catalyzed direct C2-arylation of azoles with aromatic triazenes

A highly efficient palladium-catalyzed arylation of azoles at the C2-position using 1-aryltriazenes as aryl reagents was developed. Azoles including oxazoles, thiazoles, imidazoles, 1,3,4-oxadiazoles, and oxazolines could react with 1-aryltriazenes smoothly to generate the corresponding products in good to excellent yields, and various substitution patterns were tolerated toward the reaction.

Regioselective: Ortho -functionalization of bromofluorenecarbaldehydes using TMPMgCl·LiCl

A highly regioselective functionalization of 7-bromofluorene-2-carbaldehydes, potent organic chromophores, in position C3 using a mild ortho-metallation strategy (DoM) with TMPMgCl·LiCl has been developed. This approach allows the preparation of highly functionalized fluorene derivatives by conversion of the in situ generated metalated species with various electrophiles giving a fast access to novel organic phosphorescent dyes.

Secondary Phosphine Oxide Preligands for Palladium-Catalyzed C–H (Hetero)Arylations: Efficient Access to Pybox Ligands

C–H arylations of oxazolines were accomplished with a well-defined palladium catalyst derived from a secondary bisdiamantyl phosphine oxide. The single-component secondary phosphine oxide (SPO)-palladium complex enabled C–H activations with aryl bromides

Palladium-catalyzed electrophilic C–H fluorination of arenes using oxazoline as a removable directing group

Dimethyloxazoline was rationally designed to act as a removable ortho-directing group (DG) for the palladium-catalyzed C–H electrophilic fluorination of arenes. Using NFSI as the fluorinating agent, and Pd(II), Ag(I) catalytic system, electrophilic C(sp2–H) ortho-fluorination took place on a variety of aryl substrates to afford the corresponding mono- and di-fluorinated products.

Manganese-Catalyzed Direct Nucleophilic C(sp2)-H Addition to Aldehydes and Nitriles

Herein, a manganese-catalyzed nucleophilic addition of inert C(sp2)-H bonds to aldehydes and nitriles is disclosed by virtue of a dual activation strategy. The reactions feature mild reaction conditions, excellent regio- and stereoselectivity, and a wide substrate scope, which includes both aromatic and olefinic C-H bonds, as well as a large variety of aldehydes and nitriles. Moreover, mechanistic studies shed light on possible catalytic cycles.

Analogues of doxanthrine reveal differences between the dopamine D 1 receptor binding properties of chromanoisoquinolines and hexahydrobenzo[a]phenanthridines

Efforts to develop selective agonists for dopamine D1-like receptors led to the discovery of dihydrexidine and doxanthrine, two bioisosteric β-phenyldopamine-type full agonist ligands that display selectivity and potency at D1-like receptors. We report herein an improved methodology for the synthesis of substituted chromanoisoquinolines (doxanthrine derivatives) and the evaluation of several new compounds for their ability to bind to D1- and D2-like receptors. Identical pendant phenyl ring substitutions on the dihydrexidine and doxanthrine templates surprisingly led to different effects on D1-like receptor binding, suggesting important differences between the interactions of these ligands with the D1 receptor. We propose, based on the biological results and molecular modeling studies, that slight conformational differences between the tetralin and chroman-based compounds lead to a shift in the location of the pendant ring substituents within the receptor.

C-H bond arylations and benzylations on oxazol(in)es with a palladium catalyst of a secondary phosphine oxide

An air-stable, well-defined palladium complex derived from secondary phosphine oxide (SPO) (1-Ad)2P(O)H enabled efficient C-H bond functionalizations with ample scope, which set the stage for direct arylations and benzylations of (benz)oxazoles, as well as unprecedented palladium-catalyzed C-H bond arylations on nonaromatic oxazolines.

A novel and direct synthesis of 1,3,4-oxadiazoles or oxazolines from carboxylic acids using cyanuric chloride/indium

Direct synthesis of various oxazolines and 1,3,4-oxadiazoles from carboxylic acids was achieved using cyanuric chloride/indium under very mild conditions.