Chemoselective Demethylation of Methoxypyridine

Synlett ◽  
2019 ◽  
Vol 30 (08) ◽  
pp. 951-954
Author(s):  
Kosho Makino ◽  
Yumi Hasegawa ◽  
Takahide Inoue ◽  
Koji Araki ◽  
Hidetsugu Tabata ◽  
...  
Keyword(s):  
Good Yield ◽  
Efficient Synthesis ◽  
Antiulcer Agent ◽  
Reflux Temperature

A chemoselective demethylation method for various methoxypyridine derivatives has been developed. Treatment of 4-methoxypyridine with L-selectride in THF for 2 h at reflux temperature afforded 4-hydroxypyridine in good yield; no reaction to anisole occurred. The utility of our method was demonstrated by the efficient synthesis of the metabolic substances of the antiulcer agent omeprazole. Chemoselective demethylation at the site of 3,5-dimethyl-4-methoxypyridine in the presence of 4-methoxybenzimidazole was achieved.

Efficient Synthesis of DiAZT Triphosphate

2014 ◽  
Vol 662 ◽  
pp. 59-62
Author(s):  
Shan Shan Gong ◽  
Qi Sun
Keyword(s):  
Efficient Method ◽  
Good Yield ◽  
Efficient Synthesis

A facile and efficient method for the synthesis ofP1,P3-dizidovudine-5′,5′-triphosphate has been developed. The coupling of zidovudine diphosphate with zidovudine phosphoropiperidate based on the DCI activation of P-N bond afforded the desired product in good yield.

Eine effiziente Synthesemethode für DiarylallenyIiden(pentacarbonyl)chrom- und -wolfram-Komplexe -Kristallstruktur von (CO)5Cr=C=C=CPh2 / An efficient Synthesis of Diarylallenylidene Pentacarbonyl Chromium and Tungsten Complexes - Crystal Structure of (CO)5Cr=C=C=CPh2

1994 ◽  
Vol 49 (9) ◽  
pp. 1207-1214 ◽  
Author(s):  
Helmut Fischer ◽  
David Reindl ◽  
Gerhard Roth
Keyword(s):  
Crystal Structure ◽  
Structure Analysis ◽  
Good Yield ◽  
Efficient Synthesis ◽  
X Ray ◽  
Tungsten Complexes ◽  
And Tungsten

An efficient synthesis of diarylallenylidene pentacarbonyl chromium and tungsten com­plexes is presented. Irradiation of M(CO)6 in THF affords (CO)sM[THF], Substitution of the THF ligand by diarylpropargylalcoholate and subsequent desoxygenation with COCF gives the title compounds in good yield. (The structure of diphenylallenylidene pentacarbonyl chromium has been determined by X-ray structure analysis

Efficient synthesis of 2,3-dimethoxy-5-methyl-6-morpholinomethyl-1,4-benzoquinone hydrochloride

2015 ◽  
Vol 70 (4) ◽  
pp. 221-223 ◽  
Author(s):  
Jin Wang ◽  
Teng-huo-sheng Liao ◽  
Jian Yang
Keyword(s):  
Title Compound ◽  
Good Yield ◽  
Efficient Synthesis ◽  
Reaction Sequence

AbstractThe title compound (5) was prepared by a reaction sequence starting from 2,3,4,5-tetramethoxytoluene (1) via the Blanc reaction, oxidation and alkylation. The described method provides a good yield of the C-6 heterocyclic-substituted benzoquinone derivative and is suitable for the synthesis of other benzoquinone derivatives.

An Efficient Synthesis of 2-(3-methylbutoxy)-1,3-benzodithiole

2002 ◽  
Vol 2002 (1) ◽  
pp. 11-12 ◽  
Author(s):  
Abd El-Wareth Sarhan ◽  
Taeko Izumi
Keyword(s):  
Good Yield ◽  
Efficient Synthesis

2-(3-Methylbutoxy)-1,3-benzodithiole has been synthesised in good yield by a modification of the method previously described by Nakayama.

scholarly journals Facile Iodine-Catalyzed Michael Addition of Indoles to α,α′-Bis(arylmethylene)cyclopentanones: An Efficient Synthesis of E-2-(3-Indolylphenylmethyl)-5-phenylmethylenecyclopentanones

2012 ◽  
Vol 2012 ◽  
pp. 1-6 ◽  
Author(s):  
Rammohan Pal ◽  
Arpita Das Gupta ◽  
Asok K. Mallik
Keyword(s):  
Michael Addition ◽  
Good Yield ◽  
Indole Derivatives ◽  
Efficient Synthesis ◽  
Michael Adducts

Iodine-catalyzed reaction of indoles with α,α′-bis(arylmethylene)cyclopentanones afforded one diastereomer of the corresponding Michael adducts, namely, E-2-(3-indolylphenylmethyl)-5-phenylmethylenecyclopentanones, in a good yield. The products form a new group of indole derivatives.

scholarly journals An Efficient Synthesis of 4-Aminomethyl-1-(2-Phenylethyl)-Piperidin-4-ol: A Key Intermediate in Fenspiride HCl Synthesis

2021 ◽  
pp. 139-146
Author(s):  
Prasad Panchabhai ◽  
Neelakandan Kaliaperumal ◽  
Gopalakrishnan Mannathusamy ◽  
Anbuselvan Chinnadurai
Keyword(s):  
Green Chemistry ◽  
Hazardous Waste ◽  
Building Block ◽  
Manufacturing Process ◽  
Good Yield ◽  
Aqueous Ammonia ◽  
Scale Production ◽  
Efficient Synthesis ◽  
Environment Friendly ◽  
Bulk Scale

The article confers a scalable manufacturing process of Fenspiride HCl. 4-aminomethyl-1-(2-phenylethyl)-piperidin-4-ol is the main building block in Fenspiride HCl synthesis. The reported reagents for 4-aminomethyl-1-(2-phenylethyl)-piperidin-4-ol synthesis are costly, explosive, highly toxic, produce hazardous waste, and also need to be handled with most care. The paper introduces aqueous ammonia as an alternate reagent in Fenspiride HCl and used in 4-aminomethyl-1-(2-phenylethyl)-piperidin-4-ol synthesis. The new green chemistry aspect makes the process environment-friendly and cheaper. It also eliminates toxic, sensitive, and hazardous reagents and makes the process safe on uncomplicated on bulk scale production. The high pure Fenspiride HCl is obtained by following this process and meets the ICH limits with good yield.

scholarly journals A novel methodology for the efficient synthesis of 3-monohalooxindoles by acidolysis of 3-phosphate-substituted oxindoles with haloid acids

2021 ◽  
Vol 17 ◽  
pp. 2321-2328
Author(s):  
Li Liu ◽  
Yue Li ◽  
Tiao Huang ◽  
Dulin Kong ◽  
Mingshu Wu
Keyword(s):  
Good Yield ◽  
Efficient Synthesis ◽  
Reaction Conditions ◽  
Simple Operation ◽  
Synthetic Strategy ◽  
Novel Method

A novel method for the synthesis of 3-monohalooxindoles by acidolysis of isatin-derived 3-phosphate-substituted oxindoles with haloid acids was developed. This synthetic strategy involved the preparation of 3-phosphate-substituted oxindole intermediates and SN1 reactions with haloid acids. This new procedure features mild reaction conditions, simple operation, good yield, readily available and inexpensive starting materials, and gram-scalability.

scholarly journals Bioactive Phytochemicals: Efficient Synthesis of Optically Active Substituted Flav-3-enes and Flav-3-en-3-o-R Derivatives

2017 ◽  
Vol 2017 ◽  
pp. 1-11
Author(s):  
Matthew Chilaka Achilonu ◽  
Moosa Mahmood Sedibe ◽  
Karabo Shale
Keyword(s):  
Good Yield ◽  
Biological Activities ◽  
Optically Active ◽  
Synthetic Chemistry ◽  
Efficient Synthesis ◽  
Anticancer Activities ◽  
Wide Range ◽  
Significant Interest ◽  
Bioactive Phytochemicals ◽  
Pharmacological Profiles

The structural core of flavene (2-phenyl-2H-chromene) is commonly found in plant flavonoids, which exhibit a wide range of biological activities and diverse pharmacological profiles (e.g., antioxidant and anticancer activities). Flavonoids have attracted significant interest in medicinal and synthetic chemistry. Substituted flav-3-ene 13 was exclusively synthesized by the stereoselective elimination of the O-mesyl moiety on C-3 of 5,7,3′,4′-tetramethoxyflavan-3-mesylate 12 with 1,8-diazabicyclo[5.4.0]undec-7-ene. The reaction of 5,7,3′,4′-tetramethoxyflavan-3-one 15 with ytterbium trifluoromethanesulfonate in methanol afforded a novel 3-O-substituted flav-3-ene derivative (3,5,7,3′,4′-pentamethoxyflav-3-ene) 17. The reduction of 4-(1,3,5-trihydroxybenzene)-5,7,3′,4′-tetra-O-benzylflavan-3-one 19b with hydrogen afforded a new compound: 3-hydroxy-4-(1,3,5-trihydroxybenzene)-5,7,3′,4′-tetrahydroxyflavan-3-en-3-ol 21 in good yield (95%), while the acetylation of 19a and 21 afforded the expected novel flav-3-en-3-acetoxy derivatives 20 (92%) and 22 (90%), respectively.

Intramolecular Oxidative Coupling of Aromatic Compounds. VI. An Efficient Synthesis of Some Dibenzocyclooctene Lignans

1994 ◽  
Vol 47 (5) ◽  
pp. 937 ◽  
Author(s):  
AR Carroll ◽  
WC Taylor
Keyword(s):  
Trans Isomer ◽  
Trifluoroacetic Acid ◽  
Aromatic Compounds ◽  
Oxidative Coupling ◽  
Good Yield ◽  
Reductive Coupling ◽  
Efficient Synthesis

The 1,4-diaryl-2,3-dimethylbutanes (4) and (5) were readily prepared by reductive coupling of an arylacetone precursor followed by hydrogenation. Intramolecular oxidative coupling (dichlorodicyanobenzoquinone/trifluoroacetic acid) gave dibenzocyclooctene derivatives in good yield. (�)-Deoxyschizandrin and the corresponding trans isomer, existing in two distinct conformations, were prepared.

scholarly journals A Concise and Efficient Synthesis of an Impurity, N-Desmethyl Alcaftadine from Alcaftadine: An H1 Antagonist

2019 ◽  
Vol 31 (10) ◽  
pp. 2257-2260 ◽  
Author(s):  
G. Sravya ◽  
Grigory V. Zyryanov ◽  
K. Ramaseshaiah ◽  
G. Malli Karjuna Reddy ◽  
C. Suresh Reddy ◽  
...  
Keyword(s):  
High Performance Liquid Chromatography ◽  
Liquid Chromatography ◽  
Solid State ◽  
High Performance ◽  
Simple Approach ◽  
Efficient Synthesis ◽  
Metal Free ◽  
H1 Antagonist ◽  
Reflux Temperature ◽  
Histamine Antagonist

Herein, a simple approach for the synthesis of N-desmethyl alcaftadine, an H1 histamine antagonist in solid state and its structure is presented. The reactions were performed under mild and metal free conditions at reflux temperature within a range of 65-70 ºC and the desired product N-desmethyl alcaftadine was obtained in high purity with good yield (96.42 %). It was detected by ultra-high-performance liquid chromatography (UHPLC).

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