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Rationalization of benzazole-2-carboxylate versus benzazine-3-one/ benzazine-2,3-dione selectivity switch during cyclocondensation of 2-aminothiophenols/phenols/anilines with 1,2-biselectrophiles in aqueous medium

The cyclocondensation reaction of 2-aminothiophenols with 1,2-biselectrophiles such as ethyl glyoxalate and diethyl oxalate in aqueous medium leads to the formation of benzothiazole-2-carboxylates via the 5-endo-trig process contrary to Baldwin’s rule. On the other hand, the reaction of 2-aminophenols/anilines produced the corresponding benzazine-3-ones or benzazine-2,3-diones via the 6-exo-trig process in compliance with Baldwin’s rule. The mechanistic insights of these cyclocondensation reactions using the hard-soft acid-base principle, quantum chemical calculations (density functional theory), and orbital interaction studies rationalize the selectivity switch of benzothiazole-2-carboxylates versus benzazine-3-ones/ benzazine-2,3-diones. The presence of water facilitates these cyclocondensation reactions by lowering of the energy barrier.

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The proportionality constant is the rate constant for the particular unimolecular reaction. the reaction rate is directly proportional to the concentration of the reactant. I hope my blog about 55687-23-5 is helpful to your research. Electric Literature of 55687-23-5

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COMPOUNDS FOR THE TREATMENT OF MULTI-DRUG RESISTANT BACTERIAL INFECTIONS

The present invention relates to compounds that demonstrate antibacterial activity, processes for their preparation, pharmaceutical compositions containing them as the active ingredient, to their use as medicaments and to their use in the manufacture of medicaments for use in the treatment of bacterial infections in warm-blooded animals such as humans. In particular this invention relates to compounds useful for the treatment of bacterial infections in warm-blooded animals such as humans, more particularly to the use of these compounds in the manufacture of medicaments for use in the treatment of bacterial infections in warm-blooded animals such as humans.

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Photoinitiated decarboxylative C3-difluoroarylmethylation of quinoxalin-2(1: H)-ones with potassium 2,2-difluoro-2-arylacetates in water

An efficient and green strategy for the preparation of C3-difluoroarylmethylated quinoxalin-2(1H)-one via a visible-light-induced decarboxylative C3-difluoroarylmethylation of quinoxalin-2(1H)-one with potassium 2,2-difluoro-2-arylacetate in water at room temperature was developed. This photoinduced reaction generated the desired products in good yields under simple and mild conditions.

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Potent platelet-derived growth factor-beta receptor (PDGF-betaR) inhibitors: Synthesis and structure-activity relationships of 7-[3-(cyclohexylmethyl)ureido]-3-{1-methyl-1H-pyrrolo[2,3-b]pyridin-3-yl} quinoxalin-2(1H)-one derivatives

We found previously that 7-[3-(cyclohexylmethyl)ureido]-3-{1-methyl-1H- pyrrolo[2,3-b]pyridin-3-yl}quinoxalin-2(1H)-one (7d-6) has considerable potency as a PDGF inhibitor. This compound showed potent inhibitory activity in a PDGF-induced CPA (Cell Proliferation Assay) and APA (Auto-Phosphorylation Assay) (IC50=0.05 mumol/l in CPA, 0.03 mumol/l in APA). Therefore, we tried to develop a novel and effective PDGF-betaR inhibitor by optimizing a series of its derivatives. We found that trifluoroacetic acid (TFA)-catalyzed coupling of pyrrolo[2,3-b]pyridines with quinoxalin-2-ones proceeded efficiently under mild oxidation condition with manganese(IV) oxide (MnO2) in situ, so this method was applied to prepare a series of derivatives. Results of in vitro screening of newly synthesized derivatives identified compound 7d-9 as having potent (IC50=0.014 mumol/l in CPA, 0.007 mumol/l in APA) and selective [IC50 values against vascular endothelial growth factor receptor 2 (VEGFR2, kinase domain region, KDR), epidermal growth factor receptor (EGFR), c-Met (hepatocyte growth factor receptor) and insulin growth factor I receptor (IGF-IR)/IC50 against PDGFR were each >1000] inhibitory activity. Moreover, in this series of derivatives, 7b-2 showed potent inhibitory activity toward both PDGF- and VEGF-induced signaling (PDGFR: IC50=0.004 mumol/l in CPA, 0.0008 mumol/l in APA, KDR: IC 50=0.008 mumol/l in APA). Herein we report a new and convenient synthetic method for this series of derivatives and its SAR study.

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Electrochemically dehydrogenative C-H/P-H cross-coupling: Effective synthesis of phosphonated quinoxalin-2(1: H)-ones and xanthenes

An efficient electrochemical approach for the C(sp2)-H phosphonation of quinoxalin-2(1H)-ones and C(sp3)-H phosphonation of xanthenes has been developed. The chemistry was performed in an undivided cell under constant current conditions and features a wide range of substrates, up to 99% yield and it is free of transition-metal catalysts- A nd external oxidants, thereby providing a straightforward approach for dehydrogenative C-H/P-H cross-coupling. In addition, control experiments disclose that some of the reactions may involve a radical pathway.

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Construction of C(sp2)?C(sp3) Bond between Quinoxalin-2(1H)-ones and N-Hydroxyphthalimide Esters via Photocatalytic Decarboxylative Coupling

A novel visible-light-driven decarboxylative coupling of alkyl N-hydroxyphthalimide esters (NHP esters) with quinoxalin-2(1H)-ones has been developed. This C(sp2)?C(sp3) bond-forming transformation exhibits excellent substrate generality with respect to both the coupling partners. Of note, a series of 3-primary alkyl-substituted quinoxalin-2(1H)-ones that were difficult to synthesize by previous methods could be obtained in moderate to excellent yields. Additionally, the mild conditions, easy availability of substrates, wide functional group tolerance and operational simplicity make this protocol practical in the synthesis of 3-alkylated quinoxalin-2(1H)-ones.

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Photoredox Catalyst Free, Visible Light-Promoted C3?H Acylation of Quinoxalin-2(1H)-ones in Water

A method for the synthesis of 3-acyl quinoxalin-2(1H)-ones through visible-light promoted decarboxylative acylation of alpha-oxo-carboxylic acids with quinoxalin-2(1H)-ones was developed. The reaction was performed in aqueous phase and photoredox catalyst was not required to run the process. (Figure presented.).

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The facile one pot synthesis of 6-substituted 2(1H)-quinoxalinones

Facile one pot synthesis of 6-substituted 2(1H)-quinoxalinones and these reaction mechanisms are described.The intramolecular cyclization reaction of 4′-substituted 2′-nitroacetoacetanilides in aqueous basic medium and the reduction of 6-substituted 2(1H)-quinoxalinone-4-oxide wit sodium borohydride or sodium hydrogensulfite were studied in detail

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A FACILE SYNTHESIS OF NOVEL TRICYCLIC COMPOUNDS, TETRAZOLOQUINOXALINES AND 1,2,4-TRIAZOLOQUINOXALINES

Novel 5-methyltetrazolo<1,5-a>quinoxalin-4-ones (5) and 5-methyl-1,2,4-triazolo<4,3-a>quinoxalin-4-ones (7) could be synthesized from 1-methyl-3-chloroquinoxalin-2-ones (3) and 1-methyl-3-hydrazinoquinoxalin-2-ones (6), respectively.Further extensive study was carried out to synthesize 4- or 7- substituted and 4,7-disubstituted tetrazolo<1,5-a>quinoxalines (10) and 1,2,4-triazolo<4,3-a>quinoxalines (12).

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With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.55687-23-5,6-Fluoroquinoxalin-2(1H)-one,as a common compound, the synthetic route is as follows.

55687-23-5, A solution of 6-fluoroquinoxalin-2(1H)-one & 7-fluoroquinoxalin-2(1H)-one (3 g, 18.28 mmol) in POCl3 (20 ml) was refluxed for 3 h. The solvent was evaporated under reduced pressure and the residue was diluted with cold water. The aqueous solution was basified by solid sodium carbonate and extracted with ethyl acetate. The combine organic layer was dried over anhydrous sodium sulfate, filtered and evaporated under reduced pressure to get crude compound. The crude compound was purified by silica gel chromatography (20% ethyl acetate in pet ether) to afford regioisomers as a mixture. The above mixture was separated by SFC purification to afford 2-chloro-6-fluoroquinoxaline (0.75 g, 44%) and 2-chloro-7-fluoroquinoxaline (0.65 g, 38%) as white solid. 2-chloro-6-fluoroquinoxaline: 1H NMR (400 MHz, DMSO-d6): delta ppm 8.75 (s, 1H), 8.14-8.11 (d, J=12 Hz, 1H), 7.67-7.64 (d, J=12 Hz, 1H), 7.59-7.54 (m, 1H); 19F NMR: delta ppm -107.15 (1F).

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Reference£º
Patent; Bristol-Myers Squibb Company; Hiebert, Sheldon; Rajamani, Ramkumar; Sun, Li-Qiang; Mull, Eric; Gillis, Eric P.; Bowsher, Michael S.; Zhao, Qian; Meanwell, Nicholas A.; Renduchintala, Kishore V.; Sarkunam, Kandhasamy; Nagalakshmi, Pulicharla; Babu, P. V. K. Suresh; Scola, Paul Michael; US2013/115190; (2013); A1;,
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