- Ultrasound-Promoted Synthesis of 4-Pyrimidinols and Their Tosyl Derivatives
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Ultrasound irradiation promoted the cyclocondensation of β-keto esters and amidines in good to excellent yields to form sixteen highly substituted 4-pyrimidinols. Tosylation of these compounds, in another ultrasound-promoted conversion, formed 4-pyrimidyl tosylates in high yields. The use of the developed protocol as an alternative route to 4-arylpyrimidines was illustrated with three examples of the Suzuki-Miyaura cross-coupling of the prepared tosylates with phenylboronic acid.
- Vidal, Matías,García-Arriagada, Macarena,Rezende, Marcos Caroli,Domínguez, Moisés
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p. 4246 - 4252
(2016/11/26)
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- Modulators of methyl modifying enzymes, compositions and uses thereof
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Agents for modulating methyl modifying enzymes, compositions and uses thereof are provided herein.
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Page/Page column 181; 82
(2015/12/26)
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- MODULATORS OF METHYL MODIFYING ENZYMES, COMPOSITIONS AND USES THEREOF
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Agents for modulating methyl modifying enzymes, compositions and uses thereof are provided herein
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Paragraph 00374; 00375
(2013/06/05)
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- Interaction of acetonitrile with trifluoromethanesulfonic acid: Unexpected formation of a wide variety of structures
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Interaction of acetonitrile with trifluoromethanesulfonic acid has been studied by multinuclear NMR and ESI-MS. It has been found that the interaction results in formation of a great variety of different cations and neutral compounds which is controlled by the ratio of CH3CN to TfOH. In the presence of an excess of the acid (molar ratio 1:8-14) diprotonated N-acetylacetamidine 1 is formed as the major product, which eventually transforms into protonated acetamidine 3 and acetic acid 4. At molar ratio of (1:1-2) diprotonated 2,4-dimethyl-6-methylidene-3H-1,3,5-triazine 12, tautomer of the diprotonated trimethyl-s-triazine 11, becomes the main product at an early stage of the reaction and diprotonated 1-(dimethyl-1,3,5-triazin-2-yl) prop-1-en-2-ol 15 at a later stage. In the case of a large excess of acetonitrile (4-20:1) trication 17 is formed as a result of the interaction between 11 and 12 along with some oligomers [(CH3CN) 3]n (n = 4-12). The Royal Society of Chemistry 2012.
- Salnikov, George E.,Genaev, Alexander M.,Vasiliev, Vladimir G.,Shubin, Vyacheslav G.
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supporting information; experimental part
p. 2282 - 2288
(2012/04/10)
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- CYCLOPROPANE COMPOUND
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A cyclopropane compound represented by the following formula (A) or a pharmaceutically acceptable salt thereof has orexin receptor antagonism, and therefore has a potencial of usefulness for the treatment of sleep disorder for which orexin receptor antagonism is effective, for example, insomnia: wherein Q represents —CH— or a nitrogen atom, R1a and R1b each independently represent a C1-6 alkyl group and the like, R1c represents a hydrogen atom and the like, R2a, R2b, R2c and R2d each independently represent a hydrogen atom, a halogen atom, a C1-6 alkyl group and the like, R3a, R3b and R3c each independently represent a hydrogen atom, a halogen atom and the like, and R3d represents a hydrogen atom and the like.
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Page/Page column 159-160
(2012/04/23)
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- Arylpiperazine-containing pyrimidine 4-carboxamide derivatives targeting serotonin 5-HT2A, 5-HT2C, and the serotonin transporter as a potential antidepressant
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Pyrimidine usually has good pharmacokinetic properties as a drug substance and considerable efforts have been devoted to develop pyrimidine derivatives into drug candidates. Arylpiperazine-containing pyrimidine 4-carboxamide derivatives were synthesized and evaluated for binding to serotonin receptors and transporter. Pyrimidine derivatives showed good antidepressant activity in FST (forced swimming test) animal model and also displayed no appreciable inhibitory activity against hERG channel blocking assay. Herein SAR studies of pyrimidine derivatives targeting serotonin receptors and transporter will be disclosed.
- Kim, Jong Yup,Kim, Deukjoon,Kang, Suk Youn,Park, Woo-Kyu,Kim, Hyun Jung,Jung, Myung Eun,Son, Eun-Jung,Pae, Ae Nim,Kim, Jeongmin,Lee, Jinhwa
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scheme or table
p. 6439 - 6442
(2010/11/18)
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- Synthesis of novel 5,6-substituted furo[2,3-d]pyrimidines via Pd-catalyzed cyclization of alkynylpyrimidinols with aryl iodides
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A flexible method for the synthesis of 5,6-disubstituted furo[2,3-d]pyrimidine derivatives is described. The key step is a palladium-catalyzed arylative cyclization of alkynylpyrimidinols with various aryl iodides, which gave the title compounds in 36-75% yield.
- Liu, Zhende,Li, Dewen,Li, Shukun,Bai, Donglu,He, Xuchang,Hu, Youhong
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p. 1931 - 1936
(2007/10/03)
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- 3-Amino-1H-pyrazolopyrimidines and 3-Aminoisothiazolopyrimidines as Precursors of Tricyclic Heteroaromatic Systems Containing a Bridgehead Nitrogen Atom.
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3-Amino-4-methyl-6-phenyl-1H-pyrazolopyrimidine (3a) and 3-amino-4-methyl-6-phenylisothiazolopyrimidine (9a) have been prepared.The former reacts with bromoacetone or 3-bromopentane-2,4-dione, to give tricyclic systems (1a) or (13) containing an extra pyrazole or pyrimidine ring, respectively; in each case the newly formed ring contains a bridgehead nitrogen atom, derived from N-2 of the starting material.With the same reagents, the latter undergoes an interesting ring-opening reaction, for which possible mechanisms are proposed.In contrast, 3-amino-1,2-benzisothiazole does not undergo ring fission under similar conditions, but gives rise to tricyclic compounds containing a bridgehead nitrogen atom.
- Golec, Julian M. C.,Scrowston, Richard M.
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p. 326 - 345
(2007/10/02)
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- A C-13 nuclear magnetic resonance study of the pyrimidine synthesis by the reactions of 1,3-dicarbonyl compounds with amidines and ureas
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The detailed mechanistic pathways are elucidated for the reactions of acetylacetone, methyl acetoacetate, and dimethyl malonate with a variety of amidines and ureas.In many cases the identification of a single intermediate allows the definition of the reaction path and identification of two steps.Intermediates characterized include ring-closed dihydroxytetrahydropyrimidines, dihydrohydroxypyrimidinones, open-chain enamides, and carbonyl addition compounds.
- Katritzky, Alan R.,Yousaf, Taher I.
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p. 2087 - 2093
(2007/10/02)
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- SYNTHESIS OF SUBSTITUTED 2- AND 4-HYDROXYAMINOPYRIMIDINES
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The reaction of 2- and 4-chlorine-containing alkyl(aryl)pyrimidines with hydroxylamine was studied.It was shown that, depending on the amount of hydroxylamine , N,O-dipyrimidinylhydroxyamides or the corresponding 2- and 4-hydroxyaminopyrimidines are formed together with 2- and 4-oxodihydropyrimidines.
- Moskalenko, G. G.,Sedova, V. F..,Mamaev, V. P.
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p. 1232 - 1236
(2007/10/02)
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- EXTRUSION REACTIONS-VII. FORMATION OF 2,5-DIARYL-1,4-DITHIINS AND 2-ACETONYL THIAZOLES
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ω-(2,6-Dimethyl-4-pyrimidinylthio-(4), 2-methyl-4-quinazolinylthio-(9), and 4-oxo-2-quinazolinylthio)-(10) acetophenones with hydrochloric or perchloric acid provide 2,5-diaryl-1,4-dithiins (7) whereas ω-(6-methyl-4-pyrimidinylthio)acetophenones (11) with aq HCl/HClO4 or POCl3 followed by hydrolysis provide 1-(4-aryl-2-thiazolyl)-2-propanones (12).Likewise, 2-(6-methyl-4-pyrimidinylthio)cyclohexanone (13) give the thiazole derivative (14).
- Singh, Harjit,Aggarwal, Sunil K.,Malhotra, Nageshwar
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p. 4941 - 4946
(2007/10/02)
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- Reaction of β-Aminocrotonamide with Dibasic Acid Derivatives
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Reaction of β-aminocrotonamide (1) with succinic anhydride gave β-succinamidocrotonamide (3a), which was treated with base to cyclize to 3,4-dihydro-6-methyl-4-oxo-2-pyrimidinepropanoic acid (4a).Similarly, pyrimidinepentanoic acid derivative 4b was prepared from compound 1 and glutaric anhydride.Reaction of compound 1 with dimethyl succinate in the presence of sodium methoxide gave the pyrimidine derivative 4a.Similar reaction of compound 1 with glutarate, adipate, and phthalate gave the corresponding pyrimidines 4b, 4c and 4d, while reaction of compound 1 with malon ate gave 2-hydroxypyridine derivative 11 and dimethylpyrimidinone 4e.Reaction of dimethyl fumarate with compound 1 in the presence of methoxide gave a poor yield of pyrrolopyridine derivative 13.
- Sato, Masayuki,Ogasawara, Hiromichi,Kato, Tetsuzo
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- HETEROCYCLES IN ORGANIC SYNTHESIS. PART V. A SYNTHESIS OF 2,5-DIARYL-1,4-DITHIINS
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ω-(2-Methyl-4-quinazolinylthio or 2,6-dimethyl-4-pyrimidinylthio or 4-oxo-2-quinazolinylthio)acetophenones on treatment with hydrochloric or perchloric acid provide 2,5-diaryl-1,4-dithiins.
- Singh, Harjit,Aggarwal, Sunil K.,Malhotra, Nageshwar
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p. 983 - 984
(2007/10/02)
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- 1,3-Oxazines and Related Compounds. VI. Synthesis and Some Reactions of 2,6-Disubstituted 4H-1,3-Thiazin-4-ones
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Various of 2,6-disubstituted 4H-1,3-thizin-4-ones (5) were synthesized by successive treatment of N-acylacetylcarboxamides with acid (such as 70percent perchloric acid or fluorosulfonic acid) and hydrogen sulfide.Reactions of 5 were investigated; ammonolysis with ethanolic ammonia gave the corresponding pyrimidin-4-ones; hydrolysis of 2-alkyl-1,3-thiazine derivatives yielded ring-opend N-acyl-β-mercaptocrotonamides; reduction with NaBH4 or LiALH4 afforded 3,4-dihydro-2H-1,3-thiazin-4-one derivatives.Keywords - 1,3-thiazin-4-one; 3,4-dihydro-2H-1,3-thiazin-4-one; pyrimidin-4-one; 1,3-oxazinium salt; 1,3-thiazinium salt; N-acylacetylcarboxamide; N-acyl-β-mercaptocrotonamide
- Yamamoto, Yutaka,Ohnishi, Shuhei,Azuma, Yutaka
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p. 1929 - 1935
(2007/10/02)
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- Reaction of β-Aminocrotonamide with N-Acylated Amino Acid Esters to give 2-Acylaminoalkyl-6-methylpirimidin-4(3H)-ones and Their Ring Closure with Polyphosphoric Acid (PPA)
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Reaction of β-aminocrotonamide with N-acylated amino acid esters in the presence of sodium methoxide gave 2-acylaminoalkyl-6-methylpyrimidin-4(3H)-ones, some of wich, on treatment with polyphosphoric acid (PPA), were transformed into imidazopyrimidines and imidazopyridines.
- Katagiri, Nobuya,Koshihara, Akemi,Atsuumi, Shugo,Kato, Tetsuzo
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p. 2288 - 2295
(2007/10/02)
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- REACTION OF 3-AMINOCROTONAMIDE WITH NITRILES
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The reaction of 3-aminocrotonamide (5) with some nitriles, such as acetonitrile, propiononitrile, iso-butyronitrile, and benzonitrile, gave the corresponding 2-substituted 6-methyl-4(3H)-pyrimidones (2a-2d).Phenylacetonitrile reacted with (5) to give 2-benzyl-6-methyl-4(3H)-pyrimidone (7) and 6-amino-4-methyl-5-phenyl-2(1H)-pyridone (8a).Malononitrile, however, reacted with (5) to afford 6-amino-5-cyano-4-methyl-2(1H)-pyridone (8b).
- Kato, Tetsuzo,Chiba, Takuo,Sasaki, Makoto
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p. 577 - 580
(2007/10/02)
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- TAUTOMERIC EQUILIBRIA OF 2(4)-MONOOXOPYRIMIDINES IN THE GAS PHASE, IN LOW-TEMPERATURE MATRICES AND IN SOLUTION
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IR absorption spectra, including the NH, OH and C=O stretching regions, have been recorded for 4-oxo-6-methyl- and 2-oxo-4,6-dimethyl pyrimidines and several related derivatives, in the gas phase, in low-temperature inert matrices, and in several liquid solvents.All the 4-oxopyrimidines in the gas phase, and 4-oxo-6-methylpyrimidine in low-temperature matrices, exhibit comparable populations of the keto and enol forms.By contrast the 2-oxopyrimidines are predominantly in the enol forms.Both classes of compounds are predominantly in the keto form in liquid solvent systems.The tautomeric equilibrium constant (KT) in the vapour phase for 4-oxo-2,6-dimethylpyrimidine is about 2, and for the other 4-oxopyrimidines is about 1.For 4-oxo-6-methylpyrimidine, the equilibrium constant in inert matrices varies slightly with the activity of the matrix gas, with the keto tautomer favoured in the more active matrix.From the temperature-dependence of KT, the free energy difference between the two tautomeric forms of 4-oxo-6-methylpyrimidine in the vapour phase has been calculated.Heats of vaporization have also been calculated for the various compounds and related to their abilities to associate by hydrogen bonding in the condensed phase.The UV absorption spectra of some of the foregoing have also been recorded in the gas phase, but these were of only limited value in studies of tautomeric equilibria, as compared to the IR spectra.
- Nowak, M. J.,Szczepaniak, K.,Barski, A.,Shugar, D.
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