- Synthesis and reactions of some heterocyclic azacyanines
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The one-step reaction of some amino-substituted heterocycles with diiodomethane to give azacyanines is reported. This useful reaction is of wider application than initially reported and includes the synthesis of new substituted pyrido-, isoquino-, benzimadazo-, and benzothiazoazacyanines 7. Furthermore, treatment of these azacyanines with base generally affects a facile opening of the dihydrotriazinium ring resulting in the formation of new heterocycles 10, 11, and 12, which would be difficult to prepare by other means. This reaction takes an additional direction in the case of halo-substituted azacyanines 7b/c/d where treatment with base gives rise to new interesting derivatives of dipyridotriazines 14b/c/d.
- Huang,Haddadin,Olmstead,Kurth
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- Directing Group Enables Electrochemical Selectively Meta-Bromination of Pyridines under Mild Conditions
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Without the use of catalysts and oxidants, a facile and sustainable electrochemical bromination protocol was developed. By introducing the directing groups, the regioselectivity of pyridine derivatives could be controlled at themeta-position utilizing the inexpensive and safe bromine salts at room temperature. A variety of brominated pyridine derivatives were obtained in 28-95% yields, and the reaction could be readily performed at a gram scale. By combining the installation and removing the directing group, the concept ofmeta-bromination of pyridines could be verified.
- Wu, Yanwei,Xu, Shanghui,Wang, Hong,Shao, Dongxu,Qi, Qiqi,Lu, Yi,Ma, Li,Zhou, Jianhua,Hu, Wei,Gao, Wei,Chen, Jianbin
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p. 16144 - 16150
(2021/07/19)
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- Preparation method of 2, 5-dibromo-3-methylpyridine
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The invention belongs to the field of organic synthesis, and particularly relates to a preparation method of 2, 5-dibromo-3-methylpyridine. The preparation method comprises the following steps: (1) adding 2-amino-3-methylpyridine and acetic anhydride into a four-neck flask, heating to reflux, and carrying out thin-layer chromatography tracking reaction; (2) when the temperature of a reaction liquid obtained in the step (1) is reduced to 20-25 DEG C, dropwise adding liquid bromine, reacting for 2-3 hours at 50-60 DEG C after dropwise adding of liquid bromine, adding water until all solids are dissolved, dropwise adding a sodium hydroxide solution, continuously reacting for 30 minutes after dropwise adding, and carrying out suction filtration, drying and recrystallization to obtain 2-amino-3-methyl-5-bromopyridine; and (3) adding the obtained 2-amino-3-methyl-5-bromopyridine into a hydrogen bromide solution, dropwise adding a saturated sodium nitrite solution under the catalysis of cuprous bromide, controlling the temperature to be -5 to 10 DEG C, and reacting for 2 to 4 hours to obtain 2, 5-dibromo-3-methylpyridine. The method provided by the invention has the beneficial effects ofmild reaction conditions, high yield, low cost and short process route, and is suitable for industrial production.
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- Synthesis method of (5-bromo-3-methyl-pyridine-2-yl)-methylamine
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The invention discloses a synthesis method of (5-bromo-3-methyl-pyridine-2-yl)-methylamine. The synthesis method includes: taking 2-amino-3-methylpyridine as the starting raw material, and carrying out bromination, diazotization, bromination and methylamination reactions to obtain (5-bromo-3-methyl-pyridine-2-yl)-methylamine. The method designs a brand-new synthetic route, has the characteristicsof mild reaction conditions, high product purity, and easily available starting raw material 2-amino-3-methylpyridine, and is easy for industrial production.
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Paragraph 0031-0033; 0042-0044; 0049-0051; 0056-0058
(2019/12/25)
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- Design, synthesis and biological evaluation of pyridone–aminal derivatives as MNK1/2 inhibitors
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Excessive phosphorylation of eukaryotic translation initiation factor 4E (eIF4E) plays a major role in the dysregulation of mRNA translation and the activation of tumor cell signaling. eIF4E is exclusively phosphorylated by mitogen-activated protein kinase interacting kinases 1 and 2 (MNK1/2) on Ser209. So, MNK1/2 inhibitors could decrease the level of p-eIF4E and regulate tumor-associated signaling pathways. A series of pyridone–aminal derivatives were synthesized and evaluated as MNK1/2 inhibitors. Several compounds exhibited great inhibitory activity against MNK1/2 and selected compounds showed moderate to excellent anti-proliferative potency against hematologic cancer cell lines. In particular, compound 42i (MNK1 IC50 = 7.0 nM; MNK2 IC50 = 6.1 nM) proved to be the most potent compound against TMD-8 cell line with IC50 value of 0.91 μM. Furthermore, 42i could block the phosphorylation level of eIF4E in CT-26 cell line, and 42i inhibited the tumor growth of CT-26 allograft model significantly. These results indicated that compound 42i was a promising MNK1/2 inhibitor for the potent treatment of colon cancer.
- Yuan, Xinrui,Wu, Hanshu,Bu, Hong,Zheng, Peiyuan,Zhou, Jinpei,Zhang, Huibin
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p. 1211 - 1225
(2019/02/28)
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- A 2, 5 - dibromo -3 - methyl pyridine preparation method (by machine translation)
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The invention belongs to the field of organic synthesis, in particular relates to a 2, 5 - dibromo - 3 - methyl pyridine preparation method, comprises the following steps: (1) the 2 - amino - 3 - methyl pyridine and acetic anhydride is added to the four flasks, heating to reflux, thin-layer chromatography the tracking reaction; (2) step (1) of reaction fluids in a temperature drop to 20 - 25 °C when, [...], paused, 50 - 60 °C reaction 2 - 3 h, to all solid-dissolving after adding water, sodium hydroxide solution, after adding continue to reaction 30 min, filtering, drying, recrystallize to get 2 - amino 3 - methyl - 5 - bromo pyridine; (3) the 2 - amino - 3 - methyl - 5 - bromo pyridine is added in a solution of hydrogen bromide, in the catalysis of cuprous bromide, [...] and sodium nitrite solution, temperature control in the - 5 - 10 °C, reaction 2 - 4 h, shall be 2, 5 - dibromo - 3 - methyl pyridine. The method of the invention is beneficial effect: mild reaction conditions, high yield, low cost, the process route is short, it is suitable for industrial production. (by machine translation)
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- PHENYL AND PYRIDINYL SUBSTITUTED IMIDAZOLES AS MODULATORS OF RORyT
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The present invention comprises compounds of Formula I. wherein: R1, R2, R3, R4, R5, Ra, Rb, Q1, and Q2 are defined in the specification. The invention also comprises a method of treating or ameliorating a ROR-γ-t mediated syndrome, disorder or disease, including wherein the syndrome, disorder or disease is selected from the group consisting of rheumatoid arthritis, psoriatic arthritis, and psoriasis. The invention also comprises a method of modulating RORγt activity in a mammal by administration of a therapeutically effective amount of at least one compound of Formula I.
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Paragraph 0431-0432
(2020/01/08)
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- Preparation method for 2,5-dibromo-3-methylpyridine
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The invention specifically relates to a preparation method for 2,5-dibromo-3-methylpyridine, which belongs to the field of organic synthesis. The preparation method comprises the following steps: (1) adding 2-amino-3-methylpyridine and acetic anhydride into a four-neck flask, carrying out heating to a reflux state and tracking a reaction via thin-layer chromatogram; (2) as the temperature of a reaction solution in the step (1) drops to 20 to 25 DEG C, adding liquid bromine drop by drop, then carrying out a reaction at 50 to 60 DEG C for 2 to 3 h after completion of the addition, adding water until all the solids are dissolved, then adding a sodium hydroxide solution drop by drop, continuing a reaction for 30 min after completion of the addition, and successively carrying out pumping filtration, drying and recrystallization so as to obtain 2-amino-3-methyl-5-bromopyridine; and (3) adding 2-amino-3-methyl-5-bromopyridine into a hydrogen bromide solution and under the catalysis of cuprous bromide, adding a saturated sodium nitrite solution drop by drop and carrying out a reaction at a temperature of -5 to 10 DEG C for 2 to 4 h so as to obtain 2,5-dibromo-3-methylpyridine. The method provided by the invention has the following beneficial effects: mild reaction conditions, high yield, low cost, short process route and suitability for industrial production.
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Paragraph 0012; 0016
(2016/10/07)
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- AZAINDENOISOQUINOLINE TOPOISOMERASE I INHIBITORS
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The invention described herein pertains to substituted azaindenoisoquinoline compounds, in particular 7-, 8-, 9-, and 10-azaindenoisoquinoline compounds, which are inhibitors of topoisomerase I, processes and intermediates for their syntheses, pharmaceutical compositions of the compounds, and methods of using them in the treatment of cancer.
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Paragraph 0174
(2014/02/16)
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- A mild method for the regioselective bromination of 2-aminopyridines
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An efficient and regioselective bromination of 2-aminopyridines was developed. The environmental friendly bromination occurs under mild and clean conditions using readily available 1-butylpyridinium bromide as the bromine source and hydrogen peroxide as the green oxidant.
- Xu, Tong,Zhou, Wen,Wang, Jing,Li, Xue,Guo, Jun-Wen,Wang, Bin
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supporting information
p. 5058 - 5061
(2015/01/08)
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- Azaindenoisoquinolines as topoisomerase i inhibitors and potential anticancer agents: A systematic study of structure-activity relationships
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A comprehensive study of a series of azaindenoisoquinoline topoisomerase I (Top1) inhibitors is reported. The synthetic pathways have been developed to prepare 7-, 8-, 9-, and 10-azaindenoisoquinolines. The present study shows that 7-azaindenoisoquinolines possess the greatest Top1 inhibitory activity and cytotoxicity. Additionally, the introduction of a methoxy group into the D-ring of 7-azaindenoisoquinolines improved their biological activities, leading to new lead molecules for further development. A series of QM calculations were performed on the model "sandwich" complexes of azaindenoisoquinolines with flanking DNA base pairs from the Drug-Top1-DNA ternary complex. The results of these calculations demonstrate how changes in two forces contributing to the π-π stacking (dispersion and charge-transfer interactions) affect the binding of the drug to the Top1-DNA cleavage complex and thus modulate the drug's Top1 inhibitory activity.
- Kiselev, Evgeny,Agama, Keli,Pommier, Yves,Cushman, Mark
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experimental part
p. 1682 - 1697
(2012/05/04)
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- An efficient, rapid, and regioselective bromination of anilines and phenols with 1-butyl-3-methylpyridinium tribromide as a new reagent/solvent under mild conditions
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1-Butyl-3-methylpyridinium tribromide, [BMPy]Br3 proves to be a highly efficient, regioselective reagent/solvent for nuclear bromination of various anilines and phenols. The synthesis and characterization of the room temperature ionic liquid [BMPy]Br3 (2) is described. The bromination was carried out in the absence of organic solvents and in most cases the only extraction solvent needed was water. The spent 1-butyl-3-methylpyridinium bromide (1) was easily recycled.
- Borikar, Sanjay P.,Daniel, Thomas,Paul, Vincent
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scheme or table
p. 1007 - 1009
(2009/05/11)
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- PROCESS
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The present application provides a process for the production of 7-azaindole systems by reacting a compound of formula I-1 with base
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- Synthesis of the grass alkaloid perlolidine through a pyridyne cyclisation reaction
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A synthesis of the grass alkaloid perlolidine is described in which the key step involves the pyridyne cyclisation of 2-benzyloxy-5-bromo-3-[(N-phenyl) aminomethyl] pyridine.
- Kessar,Singh
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p. 1129 - 1131
(2007/10/03)
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- Bromination of Pyridines. II. Bromination of Aminopicolines
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The bromination of all ten possible aminopicolines 1-10 was investigated.In general, the major brominated product was that corresponding to electrophilic attack at the sites para or ortho to the amino group.
- Dunn, A. D.,Currie, A.,Hayes, L. E.
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p. 369 - 374
(2007/10/02)
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