5220-59-7

Upstream product

• 1118-66-7 4-amino-3-penten-2-one 
• 60-29-7 diethyl ether 
• 15397-33-8 3-Oxo-3-phenylpropanal 
• 1131-80-2 (E)-3-(N,N-dimethylamino)-1-phenyl-2-propen-1-one 
• 123-54-6 acetylacetone 
• 25039-25-2 (Z)-1-phenyl-3-(phenylamino)prop-2-en-1-one 
• 1201-93-0 1-phenyl-3-dimethylaminoprop-2-enone 
• 2298-49-9 N-methyl-3-oxo-N-(3-oxo-3-phenylpropyl)-3-phenylpropan-1-aminium chloride 
• 50-00-0 formaldehyd 
• 19433-17-1 acetophenone O-acetyloxime 
• 93-55-0 1-phenyl-propan-1-one 

Downstream Products

• 1001890-86-3 C₁₄H₁₂BrNO 
• 1408420-75-6 (E)-3-(benzo[d][1,3]dioxol-5-yl)-1-(2-methyl-6-phenylpyridin-3-yl)prop-2-en-1-one 

Relevant academic research and scientific papers

Synthetic method of 3-acyl pyridine compound

The invention discloses a 3-acyl pyridine compound synthetic method, which belongs to the technical field of organic synthesis. The synthetic method takes an enaminone compound and an alpha, beta-saturated ketone compound or an alpha, beta-saturated aldeh

Synthesis of Functionalized Pyridines via Cu(II)-Catalyzed One-Pot Cascade Reactions of Inactivated Saturated Ketones with Electron-Deficient Enamines

In this paper, a novel and efficient synthesis of 3-acylpyridines and pyridine-3-carboxylates through the oxidative one-pot sequential reactions of inactivated saturated ketones with electron-deficient enamines is presented. Mechanistically, the formation of the title compounds involves the in situ formation of an enone intermediate through an oxidative dehydrogenation of the saturated ketone substrate, followed by its [3+3] annulation with β-enaminone or β-enaminoester via a cascade process, including Michael addition, aldol type condensation, and oxidative aromatization.

Mannich bases as enone precursors for water-mediated efficient synthesis of 2,3,6-trisubstituted pyridines and 5,6,7,8-tetrahydroquinolines

A highly efficient, regioselective, and environmentally friendly method has been developed for water-mediated synthesis of 2,3,6-trisubstituted pyridines and 5,6,7,8-tetrahydroquinolines. The introduced method allows easy preparation of various polysubstituted pyridines and 5,6,7,8-tetrahydroquinolines via domino reaction of an enolizable ketone, ammonia and enones derived from different Mannich bases in mild reaction conditions. Montmorillonite K-10 promoted this one-pot three-component reaction and gave both new and known 2,3,6-trisubstituted pyridines and 5,6,7,8-tetrahydroquinolines in good yields. The reaction protocol provides a wide array of functionality in construction of polysubstituted pyridines and 5,6,7,8-tetrahydroquinolines from commercially available starting materials in easily applicable and environmentally friendly conditions.

Cu-Catalyzed Three-Component Cascade Annulation Reaction: An Entry to Functionalized Pyridines

A concise copper-catalyzed N-O bond cleavage/C-C/C-N bond formation procedure has been described for the synthesis of multisubstituted pyridines. Various oxime acetates, activated methylene compounds, and a wide range of aldehydes bearing aryl, heteroaryl, vinyl, and trifluoromethyl groups were employed to provide the tri- or tetrasubstituted pyridines with flexible substitution patterns. Moreover, this method features inexpensive catalysts, no need for extra oxidant, and high step-enconomy, which make it pratical and attractive.

Design, synthesis and QSAR study of certain isatin-pyridine hybrids as potential anti-proliferative agents

A hybrid pharmacophore approach was adopted to design and synthesize new series of isatin-pyridine hybrids. All the newly prepared hybrids (5a-o, 8 and 11a-d) were in vitro evaluated for their anti-proliferative activity against three human cancer cell lines, namely HepG2 hepatocellular carcinoma, A549 lung cancer and MCF-7 breast cancer. Compound 8 emerged as the most active member against HepG2 cell line (ICinf50/inf = 2.5 ± 0.39 μM), with 2.7-fold increased activity than the reference drug, doxorubicin (ICinf50/inf = 6.9 ± 2.05 μM). Whilst, compound 11c was found to be the most potent counterpart against A549 and MCF-7 cell lines with ICinf50/inf values of 10.8 ± 1.15 and 6.3 ± 0.79, respectively. The weightiness of the utilization of non-cleavable linker, as the chalcone linker, and simplification of the first group, was explored via the SAR study. Furthermore, a QSAR model was built to explore the structural requirements controlling the cytotoxic activities. Notably, the predicted activities by the QSAR model were very close to those experimentally observed, hinting that this model could be safely applied for prediction of more efficacious hits comprising the same skeletal framework. Finally, a theoretical kinetic study was established to predict the ADME of the active hybrids.

Microwave assisted synthesis of 6-aryl-2-methyl-3-[benzothiazinylpyridinyl / 2-aminopyrimidinyl / 2-aminothiazolyl / triazolothiadiazinyl]pyridines

A number of new 6-Aryl-2-methyl-3-[benzothiazinylpyridinyl / 2-amino pyrimidinyl / 2-aminothiazolyl and triazolothiadiazinyl] pyridines (4 - 7) have been synthesized under microwave irradiation conditions.

Microwave-assisted regioselective one-pot synthesis of trisubstituted pyridine scaffolds using K5CoW12O40.3H 2O under solvent free conditions

(Chemical Equation Presented) A highly efficient, microwave-assisted, regioselective synthesis of 2,3-disubstituted-6-arylpyridines and new series of 7,7-dimethyl-2-aryl-5,6,7,8-tetrahydroquinoline-5-ones from enaminones in the presence of K5CoW12O40.3H2O (1.0 mol %) as heterogeneous catalyst under solvent free conditions is reported.

A highly efficient regioselective one-pot synthesis of 2,3,6-trisubstituted pyridines and 2,7,7-trisubstituted tetrahydroquinolin-5-ones using K5CoW12O40·3H2O as a heterogeneous recyclable catalyst

A systematic investigation into the regioselective one-pot, three-component condensation of enaminones 1a-g, β-dicarbonyl compounds 2a-c, and ammonium acetate in the presence of a catalytic amount of K5CoW12O40·3H2O (0.01 equiv or 1.0 mol %) under solvent free conditions, as well as in refluxing isopropanol, has been reported. The reaction was highly efficient to produce 2,3,6-trisubstituted pyridines 3a-g, 4a-g, and novel 2,7,7-trisubstituted-5,6,7,8-tetrahydroquinoline-5-ones 5a-g in excellent yields. The present procedure offers advantages of short reaction time, simple work-up, and the catalyst exhibited remarkable reusable activity.

Enaminones in heterocyclic synthesis: Synthesis and chemical reactivity of 3-anilino-1-substituted-2-propene-1- one

The 3-anilinoenones 3a,b were prepared from the corresponding 3-dimethyl-aminopropenones. The reactivity of 3a,b towards a variety of carbon and nitrogen nucleophiles as well as naphthoquinones is reported.

A facile synthesis of 2,3-disubstituted-6-arylpyridines from enaminones using montmorillonite K10 as solid acid support

A facile synthesis of 2,3-disubstituted-6-arylpyridines from enaminones using montmorillonite K10 as solid acid support is described. A facile synthesis of 2,3-disubstituted-6-arylpyridines from enaminones using montmorillonite K10 as solid acid support is reported herein.