- Selenium-catalyzed intramolecular atom- And redox-economical transformation ofo-nitrotoluenes into anthranilic acids
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Anthranilic acids (AAs) are significant basic chemicals used in pharmaceuticals, agrochemicals, dyes, fragrances,etc. Superfluous steps are always involved in obtaining AAs. Herein, we demonstrate a straightforward strategy to transform abundanto-nitrotoluenes into biologically and pharmaceutically significant AAs without any extra reductants, oxidants and protecting groups. Various sensitive groups, such as halogens, sulfide, aldehyde, pyridines, quinolines,etc., can be tolerated in this transformation. A hundred-gram-scale operation is realized efficiently with almost quantitative selenium recycling. Further mechanistic studies and DFT calculations disclosed the proposed atom-exchange processes and the key roles of the selenium species.
- Jiang, Xuefeng,Li, Yiming,Lin, Zhenyang,Wang, Yuhong,Yang, Tilong
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supporting information
p. 2986 - 2991
(2021/05/05)
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- Anthranilic acid and derivatives thereof as well as synthesis method and application thereof
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In the reaction solvent, o-methyl (hetero) aryl nitro compound is taken as a reaction raw material and is used for water. The anthranilic acid and its derivatives are synthesized by the action of a catalyst, a base and an additive. The synthetic method has the advantages of cheap and easily available raw materials, simple reaction operation, high yield and excellent functional group tolerance, and provides a simple and efficient method for synthesizing o-aminobenzoic acid which is widely used in the aspects of dyes, medicines, pesticides, spices and the like. The invention further discloses the anthranilic acid and derivatives and application thereof, and has a wide application prospect.
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Paragraph 0047-0049
(2021/09/15)
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- Discovery of Novel Tacrine-Pyrimidone Hybrids as Potent Dual AChE/GSK-3 Inhibitors for the Treatment of Alzheimer's Disease
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Based on a multitarget strategy, a series of novel tacrine-pyrimidone hybrids were identified for the potential treatment of Alzheimer's disease (AD). Biological evaluation results demonstrated that these hybrids exhibited significant inhibitory activities toward acetylcholinesterase (AChE) and glycogen synthase kinase 3 (GSK-3). The optimal compound 27g possessed excellent dual AChE/GSK-3 inhibition both in terms of potency and equilibrium (AChE: IC50 = 51.1 nM; GSK-3β: IC50 = 89.3 nM) and displayed significant amelioration on cognitive deficits in scopolamine-induced amnesia mice and efficient reduction against phosphorylation of tau protein on Ser-199 and Ser-396 sites in glyceraldehyde (GA)-stimulated differentiated SH-SY5Y cells. Furthermore, compound 27g exhibited eligible pharmacokinetic properties, good kinase selectivity, and moderate neuroprotection against GA-induced reduction in cell viability and neurite damage in SH-SY5Y-derived neurons. The multifunctional profiles of compound 27g suggest that it deserves further investigation as a promising lead for the prospective treatment of AD.
- Yao, Hong,Uras, Giuseppe,Zhang, Pengfei,Xu, Shengtao,Yin, Ying,Liu, Jie,Qin, Shuai,Li, Xinuo,Allen, Stephanie,Bai, Renren,Gong, Qi,Zhang, Haiyan,Zhu, Zheying,Xu, Jinyi
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p. 7483 - 7506
(2021/06/28)
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- Copper(ii)-catalyzed c-n coupling of aryl halides and n-nucleophiles promoted by quebrachitol or diethylene glycol
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Herein, we report the natural ligand quebrachitol (QCT) as a promoter for a Cu(II) catalyst, which is highly effective for N-Arylation of various amines and related aryl halides. A series of diarylamine derivatives were obtained in high yields by using diethylene glycol (DEG) as both ligand and solvent. The C-N coupling reactions proceed under mild conditions and exhibit good functional group tolerance.
- Chen, Guoliang,Chen, Yuanguang,Du, Fangyu,Fu, Yang,Wu, Ying,Zhou, Qifan
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supporting information
p. 2161 - 2168
(2019/11/25)
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- Br?nsted Acid-Catalyzed Asymmetric Ring-Closing Alkylation of Inert N-substituted Pyrroles with α, β-Unsaturated Ketones
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A Chiral Br?nsted acid catalyzed asymmetric intramolecular ring-closing alkylation of inert pyrroles with α, β-unsaturated ketones has been developed. This approach gave a wide range of 4-phenyl-4,5-dihydro-6H-benzo[f]pyrrolo[1,2-a]azepin-6-ones in high yields with good enantioselectivities under mild reaction conditions. (Figure presented.).
- Wei, Zhao,Zhang, Jinlong,Yang, Huameng,Jiang, Gaoxi
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supporting information
p. 3694 - 3697
(2019/07/12)
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- Efficient construction of 3-substituted-quinazolin-4(3H)-ones and theoretical investigation on the reaction pathways
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A highly efficient and convenient method was developed to synthesize 2,7-dimethyl-3- phenyl- quinazolin-4(3H)-ones from 2-acetamidobenzoic acid, arylamines, arylhydrazines and arylacylhydrazines. Quinazolin-4(3H)-ones were obtained in good to excellent yields (85–98%) using dropwise POCl3 as a condensing agent in acetonitrile. Theoretical calculations were performed to explore the competition reaction pathways and the corresponding free energy profiles for the reaction of 2-acetamido-4-methyl-benzoic acid with aniline. The calculations show that the reaction proceeds through three different stages, including the formation of benzoxazin-4-one, diamide and quinazolin-4(3H)-one. The formation of benzoxazin-4-one follows a Vilsmeier-Haack mechanism, in which the POCl3 transfers the 2-acetamido-benzoic acid into an imidoyl chloride, followed by intramolecular attack of the carboxyl oxygen involving addition-elimination sequence. The formation of diamide is initialized by the nucleophilic attack of the aniline nitrogen atom on the carbonyl carbon of benzoxazin-4-one, accompanied by aniline-assisted proton transferring. The formation of quinazolin-4(3H)-one follows an intramolecular nucleophilic addition-elimination mechanism, where the POCl3 helps the elimination of water. The present studies provide insight into the mechanism for the formation reactions of quinazolin-4(3H)-ones in the presence of POCl3.
- Zhao, Xinyun,Lu, Juanfeng,Wu, Lamei,Chen, Xi
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p. 1040 - 1047
(2017/09/08)
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- On the Synthesis and Reactivity of 2,3-Dihydropyrrolo[1,2- a ]quinazolin-5(1 H)-ones
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An improved, scalable synthetic route to the quinazolinone natural product 2,3-dihydropyrrolo[1,2-a]quinazolin-5(1H)-one is reported. The applicability of this method to analogue synthesis and the synthesis of related natural products is explored. Finally, reactivity of the scaffold to a variety of electrophilic reagents, generating products stereoselectively, is reported.
- Sutherell, Charlotte L.,Ley, Steven V.
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supporting information
p. 135 - 144
(2016/12/24)
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- The Synthesis of 5-Amino-dihydrobenzo[b]oxepines and 5-Amino-dihydrobenzo[b]azepines via Ichikawa Rearrangement and Ring-Closing Metathesis
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The combination of Ichikawa's rearrangement and a ring-closing metathesis reaction of allyl carbamates is presented as a method for the preparation of 5-amino-substituted 2,5-dihydro-benzo[b]oxepines, 2,5-dihydro-benzo[b]azepines, and 2,5-dihydro-benzo[b]thiepins. It was demonstrated that the use of nonracemic allyl carbamates enables the synthesis of enantioenriched benzo-fused seven-membered heterocycles. Finally, it was shown that further functionalization of the obtained structures allows access to pharmacologically active 5-amino-substituted 2,3,4,5-tetrahydro-1-benzo[b]oxepine scaffolds.
- Chwastek, Monika,Pieczykolan, Micha?,Stecko, Sebastian
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p. 9046 - 9074
(2016/10/17)
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- Synthesis method of 3-amino-6-chloro-N,4-dimethylbenzamidedimethyl formamide
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The invention relates to a synthesis method of a compound, in particular to a synthesis method of 3-amino-6-chloro-N,4-dimethylbenzamidedimethyl formamide. The method comprises the following steps of adopting 3-nitro-4methyl benzoic acid and sodium hydroxide as raw materials, obtaining yellowish powder through ferric chloride and a hydrazine hydrate reaction, then adding pyridine and acetonitrile, mixing uniformly, adding acetic acid, continuously stirring, adding methylamine water, carrying out extraction separation on an organic phase and sulfonyl chloride and an acetonitrile reaction after water bath reaction, obtaining filter residues after filtration, and drying to obtain the 3-amino-6-chloro-N,4-dimethylbenzamidedimethyl formamide. The method is moderate in reaction condition and high in yield.
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Paragraph 0004; 0006; 0007
(2016/11/17)
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- Highly stereoselective chemoenzymatic synthesis of the 3 h -isobenzofuran skeleton. access to enantiopure 3-methylphthalides
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A straightforward synthesis of (S)-3-methylphthalides has been developed, with the key asymmetric step being the bioreduction of 2-acetylbenzonitriles. Enzymatic processes have been found to be highly dependent on the pH value, with acidic conditions being required to avoid undesired side reactions. Baker's yeast was found to be the best biocatalyst acting in a highly stereoselective fashion. The simple treatment of the reaction crudes with aqueous HCl has provided access to enantiopure (S)-3-methylphthalides in moderate to excellent yields.
- Mangas-Sanchez, Juan,Busto, Eduardo,Gotor-Fernandez, Vicente,Gotor, Vicente
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supporting information; experimental part
p. 1444 - 1447
(2012/06/01)
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- Pyridazinedione compounds useful in treating neurological disorders
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The present invention relates to pyridazino[4,5-b]quinolines, and pharmaceutically useful salts thereof, which are excitatory amino acid antagonists and which are useful when such antagonism is desired such as in the treatment of neurological disorders. The invention further provides pharmaceutical compositions containing pyridazino[4,5-b]quinolines as active ingredient, and methods for the treatment of neurological disorders.
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- Bisazo brown reactive dye
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A brown reactive dye represented by a free acid of the formula, STR1 wherein R is a hydrogen atom or a C1 to C4 alkyl group, X is --SO2 CH2 CH2 Cl, --SO2 CH=CH2, --SO2 CH2 CH2 OSO3 H or --SO2 CH2 CH2 OPO3 H2, rings A, B and C are each a benzene or naphthalene ring which may have other substituent, m is 0 to 3 and n is 0 to 1. This dye is suitable for dyeing cellulose fibers brown to afford dyeings superior in fastnesses, acid stability, build-up property and level dyeing property.
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