- One-Pot, Tandem Wittig Hydrogenation: Formal C(sp3)-C(sp3) Bond Formation with Extensive Scope
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A one-pot, tandem Wittig hydrogenation of aldehydes with stabilized ylides is reported, representing a formal C(sp3)-C(sp3) bond construction. The tandem reaction operates under mild conditions, is high yielding, and is broad in scope. Chemoselectivity for olefin reduction is observed, and the methodology is demonstrated in the synthesis of lapatinib analogues and a formal synthesis of (±)-cuspareine. Early insights suggest that the chemoselectivity observed in the reduction step is due to partial poisoning of the catalyst, after step one, thus adding to the power of the one-pot procedure.
- Devlin, Rory,Jones, David J.,Mcglacken, Gerard P.
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- Preparation method of medium-and-long chain fatty carboxylic acid
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The application discloses a preparation method of medium-and-long chain fatty carboxylic acid. More specifically, the preparation method comprises the following steps: taking 2-halogenated methylfuranas a raw material; in the presence of a metal reagent a
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Paragraph 0040-0044
(2019/04/04)
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- Structure-Odor Correlations in Homologous Series of Mercapto Furans and Mercapto Thiophenes Synthesized by Changing the Structural Motifs of the Key Coffee Odorant Furan-2-ylmethanethiol
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Furan-2-ylmethanethiol (2-furfurylthiol; 2-FFT, 1) is long-known as a key odorant in roast and ground coffee and was also previously identified in a wide range of thermally treated foods such as meat, bread, and roasted sesame seeds. Its unique coffee-like odor quality elicited at very low concentrations, and the fact that only a very few compounds showing a similar structure have previously been described in foods make 1 a suitable candidate for structure-odor activity studies. To gain insight into the structural features needed to evoke a coffee-like odor at low concentrations, 46 heterocyclic mercaptans and thio ethers were synthesized, 32 of them for the first time, and their odor qualities and odor thresholds were determined. A movement of the mercapto group to the 3-position kept the coffee-like aroma but led to an increase in odor threshold. A separation of the thiol group from the furan ring by an elongation of the carbon side chain caused a loss of the coffee-like odor and also led to an increase in odor thresholds, especially for ω-(furan-2-yl)alkane-1-thiols with six or seven carbon atoms in the side chain. A displacement of the furan ring by a thiophene ring had no significant influence on the odor properties of most of the compounds studied, but the newly synthesized longer-chain 1-(furan-2-yl)- and 1-(thiophene-2-yl)alkane-1-thiols elicited interesting passion fruit-like scents. In total, only 4 out of the 46 compounds also showed a coffee-like odor quality like 1, but none showed a lower odor threshold. Besides the odor attributes, also retention indices, mass spectra, and NMR data of the synthesized compounds were elaborated, which are helpful in possible future identification of these compounds in trace levels in foods or other materials.
- Schoenauer, Sebastian,Schieberle, Peter
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p. 4189 - 4199
(2018/05/01)
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- NOVEL COMPOUNDS
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There is provided a compound of formula (I): or a pharmaceutically acceptable salt thereof. There are also provided processes for the manufacture of a compound of Formula 1, and the use of a compound of Formula 1 as a medicament and in the treatment of cancer.
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Page/Page column 96
(2008/12/06)
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- Novel Compounds
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There is provided a compound of formula (I): processes for the manufacture thereof, pharmaceutical compositions thereof and uses in therapy.
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Page/Page column 110
(2008/06/13)
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- Iridium catalysts with bicyclic pyridine-phosphinite ligands: Asymmetric hydrogenation of olefins and furan derivatives
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(Chemical Equation Presented) Superior bicyclics: Iridium catalysts as 1 derived from pyridine-phosphinite ligands considerably extend the scope of asymmetric hydrogenation. In addition to various unfunctionalized and functionalized olefins, furans, and benzofurans, for which no catalysts were known before, are also hydrogenated with high enantioselectivity (see scheme).
- Kaiser, Stefan,Smidt, Sebastian P.,Pfaltz, Andreas
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p. 5194 - 5197
(2007/10/03)
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- 3-heteroarylalkyl substituted gaba analogs
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The invention is a novel series of compounds which are useful in the treatment of epilepsy, faintness attacks, neurodegenerative disorders, depression, anxiety, panic, pain, neuropathological disorders, gastrointestinal disorders such as irritable bowel syndrome (IBS), and inflammation, especially arthritis. A pharmaceutical composition containing a compound of the invention as well as methods of preparing the compounds and novel intermediates useful in the preparation of the final compounds are included.
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Page column 30
(2010/02/05)
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- Synthetic approach towards nakadomarin A: Efficient synthesis of the central tetracyclic core
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An efficient synthesis of the tetracyclic core of nakadomarin A was accomplished starting from methyl 4-oxo-3-piperidinecarboxylate. The key steps were intramolecular cyclization of furan to N-acyliminium ions to construct the strained central cyclopenten
- Nagata, Toshiaki,Nishida, Atsushi,Nakagawa, Masako
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p. 8345 - 8349
(2007/10/03)
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- Structure-Odor Correlation, XXI. Olfactory Properties and Convenient Synthesis of Furans and Thiophenes Related to Rose Furan and Perillene and Their Isomers
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Starting from 3-bromofuran (1) or 3-bromothiophene (2) via alkylation in 2-position (-> 3-8) followed by the corresponding second alkylation in 3-position, we obtained rose furan (9), rose thiophene (10), and their analogs 11-16.From the α,β-unsaturated esters 17-20 by hydrogenation (-> 21-24), DIBAH reduction (-> 25-28), and Wittig reaction, perillene (29), thioperillene (30), and their analogs 29-36 were obtained.Olfactory evaluation showed that the difference between the furans and thiophene derivatives is remarkably small, particularly for perillene (29) compared with thioperillene (30), and their analogs.Also the influence of position and structure of the side chain is lower than expected within the compared compounds 9-36. - Keywords: Rose furan / Perillene / Furans / Thiophenes / Structure-odor correlation / Odoriferous substances
- Weyerstahl, Peter,Schenk, Anja,Marschall, Helga
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p. 1849 - 1854
(2007/10/03)
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- Lewis acid-promoted alkylations of arenes and 1-trimethylsilylalkynes with β-chloro-β-thiopropanoic esters
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Ethyl 3-chloro-3-(3,4-dichlorophenylthio)propanoate (8) reacted with electron-rich arenes in the presence of titanium tetrachloride to give the Friedel-Crafts products 10a-13a. Reactions of 8 with 1-trimethylsilylalkynes 14a-d were effected with aluminum chloride to afford the substitution products 15a-d. Some chemical transformations of the products are also described.
- Ishibashi,Mino,Sakata,Inada,Ikeda
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p. 1148 - 1151
(2007/10/02)
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- Isocytosine H2-receptor histamine antagonists II. Synthesis and evaluation of biological activity at histamine H1- and H2-receptors of 5-(heterocyclyl)methylisocytosines
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A series of 2--4-pyrimidones was synthesized based on oxmetidine 2, in which the methylenedioxyphenyl group of 2 was replaced by a heterocyclic ring.Good H2-receptor antagonist activity was retained over a range of basic and neutral heterocyclic substituents.Replacement of the 5-methyl-4-imidazolyl ring in selected compounds with 2-thiazolyl and, particularly, 3-bromo-2-pyridyl rings gave a series of compounds which have both H1- and H2-receptor histamine antagonist activities.Some structure-activity and structure-toxicity correlations are discussed.Compound 6d, 2--5-(6-methylpyrid-3-yl)-4-pyrimidone, has the most favourable combination of properties for H2-antagonism and has been evaluated further as an anti-secretory agent.
- Brown, Thomas H.,Blakemore, Robert C.,Blurton, Peter,Durant, Graham J.,Ganellin, C. Robin,et al.
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- PHENYL ALKYLAMINOPYRIMIDONES
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The compounds are phenyl alkylaminopyrimidones which are histamine H. sub.2-antagonists. A specific compound of the present invention is 2-[2-[3-(dimethylaminomethyl)benzylthio]ethylamino]-5-(6-methyl-3-pyridylme thyl)-4-pyrimidone.
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- AN IMPROVED PROCEDURE FOR HYDROSILATION OF α,β-UNSATURATED ESTERS AND AN EXTENSION TO CONJUGATED DIENE ESTERS
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Treatment of α,β-unsaturated esters with triethylsilane in benzene in the presence of a catalytic amount of tris(triphenylphosphine)rhodium chloride at room temperature followed by chromatography on silica gel give rise to the corresponding saturated esters.Under similar conditions, fully conjugated diene esters were reduced to the dihydrolevel to give β,γ- or γ,δ-unsaturated esters depending upon the substitution pattern of the starting substrate.
- Liu, Hsing-Jang,Ramani, Brahma
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p. 965 - 972
(2007/10/02)
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- PYRIMIDONES HAVING HISTAMINE H2-ANTAGONIST ACTIVITY
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The compounds of this invention are 5-dialkylaminoalkylfuranyl (or thienyl, phenyl or pyridyl)!-4-pyrimidones having histamine H 2-antagonist activity. A specific compound of this invention is 2-2-(5-dimethylaminomethyl-2-furanylmethylthio) ethylamino!-5-(5-dimethylamino methyl-2-furanylmethyl)-4-pyrimidone.
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- ISOUREAS AND ISOTHIOUREAS
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The compounds are isoureas and isothioureas which have an O-or S-alkylpyrimidone substituent and which are histamine H 2-antagonists and antiinflammatory agents. A specific compound of this invention is 2-[5-(O-isoureido)pentylamino]-5-(6-methyl-3-pyridylmethyl)-4-pyrimidone.
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- Pyrimidine compounds
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The compounds are substituted pyrimidine compounds which are histamine H2 -antagonists. A specific compound of the present invention is 2-[2-(5-dimethylaminomethyl)-2-furylmethylthio)ethylamino]-5-(3-pyridylmethyl)-4-pyrimidone.
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