67823-03-4

Upstream product

• 13329-40-3 4-Iodoacetophenone 

Downstream Products

• 1178563-01-3 5-(4-hydroxy-2-oxo-2H-chromen-3-yl)-4-(4-iodophenyl)-2,3-dihydro-1H-imidazol-2-one 
• 1063627-08-6 8,10-dimethyl-4-(4-iodophenyl)-1,3,8,10-tetraazaspiro[5,5]-undec-4-ene-2,7,9,11-tetraone 
• 1063626-96-9 5-(2-(4-iodophenyl)-2-oxoethylidene)-1,3-dimethylpyrimidine-2,4,6-trione 

Relevant academic research and scientific papers

Synthesis and reactions of ethyl 6-aryl-3-ethoxy-6-oxo-2,4-hexadienoates

Biologically interesting ethyl 6-aryl-3-ethoxy-6-oxo-2,4-hexadienoates (I) have been prepared by the Wittig reaction of [3-(ethoxycarbonyl)-2-ethoxy-2- propenylidene]triphenylphosphoranes (3a and 3b) and -arsorane (3c) with glyoxal monohydrates (5) and by oxidation of 6-aryl-3-ethoxy-6-hydroxy-2,4- hexadienoate (9) with activated manganese (IV) oxide supported by silica. Reaction of la with 3c gave 3-(4-chlorobenzoyl)-1,2-trans (and cis)-bis(1- ethoxy-2-ethoxycarbonylethenyl)cyclopropanes (6 and 7). When l a was treated with a 1: 5 mixture of concentrated HCI and tetrahydrofuran at room temperature, 3-hydroxy-6-oxo-2,4-hexadienoate (10a) was obtained in 46% yield. Treatment of 1b with trifluoroacetic acid Rave 5,6-dihydro-2H-pyran- 2-one (12) in 53% yield together with [0b in 28% yield. When la was treated with 1 N ethanolic potassium hydroxide, 12 and 2H-pyran derivative (13) were obtained in 33% and 28% yields, respectively. Reaction of la with ammonium hydroxide and primary amines in the presence of a proton acid gave 2-oxo- 1,2,5,6-tetrahydropyridines; (14) in good yields. The mechanism of the formation of 6, 12, 13, and 14 is discussed.

Ynonylation of Acyl Radicals by Electroinduced Homolysis of 4-Acyl-1,4-dihydropyridines

Herein we report the conversion of 4-Acyl-1,4-dihydropyridines (DHPs) into ynones under electrochemical conditions. The reaction proceeds via the homolysis of acyl-DHP under electron activation. The resulting acyl radicals react with hypervalent iodine(III) reagents to form the target ynones or ynamides in acceptable yields. This mild reaction condition allows wider functionality tolerance that includes halides, carboxylates, or alkenes. The synthetic utility of this methodology is further demonstrated by the late-stage modification of complex molecules.

OFF-ON-OFF Red-Emitting Fluorescent Indicators for a Narrow pH Window

A unique combination of two independent mechanisms of fluorescence quenching, namely intramolecular charge transfer (ICT) from a peripheral donor and protonation of azomethine nitrogen atoms in zinc tetrapyrazinoporphyrazines (TPyzPz), provides a new possibility for sensing pH in a specific range. The pH selectivity was controlled by the different basicities of the donor for ICT (dimethylaminoaryl), which was connected to the macrocycle by π-extended linkers of different lengths. ICT and protonation have been studied in detail by photophysical, spectral (UV/Vis and MCD spectra), and electrochemical measurements, and further supported by theoretical calculations (DFT, TDDFT). The pH-sensing properties of the TPyzPzs have been investigated in THF and in water after anchoring the TPyzPzs to liposomes. The salient pKavalues were around 1.3 (azomethine nitrogen) and 2.29–4.76 (donor for ICT). The lead indicators (sensing over a pH range of 1.0–2.5) with fairly steep sensing profiles exhibited increases in fluorescence between the OFF/ON states of more than 20-fold and strong absorption in the red region (Q-band maximum >650 nm, ?≈2×106m?1cm?1).

Syntheses, Cholinesterases Inhibition, and Molecular Docking Studies of Pyrido[2,3-b]pyrazine Derivatives

Cholinesterases, acetylcholinesterase (AChE) and butyrylcholinesterase (BChE), have a role in cholinergic deficit which evidently leads to Alzheimer's disease (AD). Inhibition of cholinesterases with small molecules is an attractive strategy in AD therapy. This study demonstrates synthesis of pyrido[2,3-b]pyrazines (6a-6q) series, their inhibitory activities against both cholinesterases, AChE and BChE, and molecular docking studies. The bioactivities data of pyrido[2,3-b]pyrazines showed 3-(3′-nitrophenyl)pyrido[2,3-b]pyrazine 6n a potent dual inhibitor among the series against both AChE and BChE with IC50 values of 0.466 ± 0.121 and 1.89 ± 0.05 μm, respectively. The analogues 3-(3′-methylphenyl)pyrido[2,3-b]pyrazine 6c and 3-(3′-fluorophenyl)pyrido[2,3-b]pyrazine 6f were found to be selective inhibition for BChE with IC50 values of 0.583 ± 0.052 μm and AChE with IC50 value of 0.899 ± 0.10 μm, respectively. Molecular docking studies of the active compounds suggested the putative binding modes with cholinesterases. The potent compounds among the series could potentially serves as good leads for the development of new cholinesterase inhibitors. A series of pyrido[2,3-b]pyrazine (6a-6q) derivatives has been synthesized and evaluated for inhibitory activities against cholinesterases; acetylcholinesterase, and butyrylcholinesterase. Molecular docking of active compounds was also performed to suggest the putative binding modes with cholinesterases.

One-pot three-component reactions of methyl ketones, phenols and a nucleophile: An expedient way to synthesize densely substituted benzofurans

Three-component reactions of phenylglyoxal monohydrate, phenols, and indoles were developed with the aid of acid-catalyst, which produced various densely substituted benzofurans with good to excellent yields. On the basis of this observation, a one-pot, step-wise reaction was developed by using methyl ketones instead of using phenylglyoxal component in I2/DMSO system. At last, three-component reaction offered a useful way to synthesize densely substituted benzofurans starting from simple and easily available substrates. The indole component can be replaced by some other nucleophiles, such as 1,2,4-trimethoxybenzene and thiophenol.