21 results match your criteria Synthetic Communications [Journal]

  • Page 1 of 1

A General Method for Nucleophilic Aromatic Substitution of Aryl Fluorides and Chlorides with Dimethylamine using Hydroxide-Assisted Decomposition of N,N-Dimethylforamide.

Synth Commun 2016;46(5):475-481. Epub 2016 Feb 9.

Department of Physical and Life Sciences, Nevada State College, Henderson, NV 89002.

A practical and convenient procedure for the nucleophilic aromatic substitution of aryl fluorides and chlorides with dimethylamine was developed using a hydroxide assisted, thermal decomposition of N,N-dimethylforamide. These conditions are tolerant of nitro, nitrile, aldehyde, ketone, and amide groups but will undergo acyl substitution to form amides for methyl esters and acyl chlorides. Isolated yields of the products range from 44 - 98%, with the majority being greater than 70% for seventeen examples. Read More

View Article

Download full-text PDF

Source
http://www.tandfonline.com/doi/full/10.1080/00397911.2016.11
Publisher Site
http://www.ncbi.nlm.nih.gov/pmc/articles/PMC5036528PMC
http://dx.doi.org/10.1080/00397911.2016.1147051DOI Listing
February 2016
27 Reads

Synthesis of indolo[4,3-]phenanthridine-6,11(2,12)-diones using the Schiff base-homophthalic anhydride cyclization reaction.

Synth Commun 2016 16;46(23):1902-1908. Epub 2016 Sep 16.

Department of Medicinal Chemistry and Molecular Pharmacology, College of Pharmacy, Purdue University and the Purdue Center for Cancer Research, West Lafayette, Indiana 47907, United States.

A novel indolophenanthridine ring system has been synthesized via the Schiff base-homophthalic anhydride cyclization followed by thionyl chloride-mediated dehydrogenation and intramolecular Friedel-Crafts acylation. This adds to the array of heterocyclic systems that are available through the cycloaddition reaction of imines with cyclic dicarboxylic acid anhydrides. The cytotoxicities of the indolophenanthridines were investigated in human cancer cell cultures, and the results documented significant antitumor activity in a variety of human cancer cell lines. Read More

View Article

Download full-text PDF

Source
http://dx.doi.org/10.1080/00397911.2016.1232409DOI Listing
http://www.ncbi.nlm.nih.gov/pmc/articles/PMC5646376PMC
September 2016
23 Reads

SYNTHETICALLY USEFUL INTERMEDIATES BY DIAZOSULFONE AND SULFONATE C-H INSERTION.

Synth Commun 2015 Jan;45(2):226-231

University of North Dakota, Chemistry Department, 151 Cornell St. Stop 9024, Grand Forks, ND, 58202, USA.

Intramolecular C-H insertion on diazosulfone and diazosulfonate substrates was used to prepare synthetically useful intermediates from easily available starting materials. Read More

View Article

Download full-text PDF

Source
http://www.tandfonline.com/doi/abs/10.1080/00397911.2014.960
Publisher Site
http://dx.doi.org/10.1080/00397911.2014.960937DOI Listing
http://www.ncbi.nlm.nih.gov/pmc/articles/PMC4278664PMC
January 2015
12 Reads

Rapid synthesis of alkoxyamine hydrochloride derivatives from alkyl bromide and di--butoxycarbonylhydroxylamine ((Boc)NOH).

Synth Commun 2014 Aug;44(16):2344-2347

National Institute of Diabetes and Digestive and Kidney Diseases, National Institutes of Health, Bethesda, MD 20892.

The conventional route to alkoxyamine hydrochloride derivatives is by reaction of alkyl bromides with -hydroxyphthalimide or -hydroxysuccinimide followed by addition of hydrazine and HCl. Transformation of an alkyl bromide to the corresponding alkoxyamine hydrochloride can be accomplished more rapidly in high yield and without using hazardous hydrazine by reaction of (Boc)NOH (di--butoxycarbonylhydroxylamine) and alkyl bromide followed by addition of HCl. Alkoxyamine hydrochlorides are powerful reagents in organic synthesis that can be used to synthesize alkoxyimino derivatives after condensation with a ketone or aldehyde. Read More

View Article

Download full-text PDF

Source
http://dx.doi.org/10.1080/00397911.2014.895014DOI Listing
http://www.ncbi.nlm.nih.gov/pmc/articles/PMC4215731PMC
August 2014
15 Reads
1 Citation
0.930 Impact Factor

Synthesis of -Diethylbenzamides via a Non-Classical Mitsunobu Reaction.

Synth Commun 2014 Jan;44(7):976-980

Department of Chemistry, Sewanee: The University of the South, 735 University Avenue, Sewanee, TN 37383-1000, USA.

The use of the Mitsunobu reaction for the synthesis of N,N-diethylbenzamides affords ortho-, meta-, and para-substituted benzamides, containing both electron-donating and electron-withdrawing groups. While the preparation of numerous functional groups has been efficiently demonstrated employing the Mitsunobu reaction, our methodology represents the first application of the Mitsunobu reaction for the construction of benzamides using benzoic acid and amine starting materials. Moreover, this synthetic transformation is believed to proceed via a non-classical mechanism involving the existence of an acyloxyphosphonium ion. Read More

View Article

Download full-text PDF

Source
http://dx.doi.org/10.1080/00397911.2013.839796DOI Listing
http://www.ncbi.nlm.nih.gov/pmc/articles/PMC4159177PMC
January 2014
32 Reads

PRACTICAL SYNTHESIS OF AROMATIC DITHIOCARBAMATES.

Synth Commun 2014;44(16):2336-2343

Department of Chemistry, Purdue University, West Lafayette, Indiana, USA.

Oxidation-sensitive N,N-diaryl dithiocarbamates (DTCs) are synthesized in good yields by the generation of metal amide salts from N-benzoyl precursors, followed by addition of CS. para-Substituted diphenylamines are prepared by electrophilic aromatic substitution of diphenylbenzamide and saponification. Deacylation of electron-rich species such as bis(p-dimethylaminophenyl)benzamide is challenging because of the oxidative sensitivity of the anionic intermediate but could be achieved in good yield by using n-BuLi to generate a hemiaminal adduct, prior to acidification. Read More

View Article

Download full-text PDF

Source
http://dx.doi.org/10.1080/00397911.2014.894527DOI Listing
http://www.ncbi.nlm.nih.gov/pmc/articles/PMC4437221PMC
January 2014
4 Reads

IMPROVED SYNTHESIS OF 10-(2-ALKYLAMINO-2-OXOETHYL)-1,4,7,10-TETRAAZACYCLODODECANE-1,4,7-TRIACETIC ACID DERIVATIVES BEARING ACID-SENSITIVE LINKERS.

Synth Commun 2014 ;44(3)

Department of Medical Imaging, University of Arizona, Tucson, AZ 85721-0041 USA ; Arizona Cancer Center, University of Arizona, Tucson, AZ 85721-0041 USA.

Alkylation of the hydrobromide salts of 1,4,7-tris(methoxycarbonylmethyl)-1,4,7,10-tetraazacyclododecane and 1,4,7-tris(ethoxycarbonylmethyl)-1,4,7,10-tetraazacyclododecane with appropriate α-bromoacetamides, followed by hydrolysis, provides convenient access to 10-(2-alkylamino-2-oxoethyl)-1,4,7,10-tetraazacyclododecane-1,4,7-triacetic acid derivatives that contain acid-sensitive functional groups. The utility of the method is demonstrated by improved syntheses of two known DOTA monoamides bearing acid-sensitive ω-tritylthio alkyl chains in much higher yields based on cyclen as the starting material. Read More

View Article

Download full-text PDF

Source
http://www.tandfonline.com/doi/abs/10.1080/00397911.2013.813
Publisher Site
http://dx.doi.org/10.1080/00397911.2013.813547DOI Listing
http://www.ncbi.nlm.nih.gov/pmc/articles/PMC3866964PMC
January 2014
24 Reads

Syntheses of Benzo[]furan-6-carbonitrile and 6-Cyanobenzo[]furan-2-boronic Acid Pinacol Ester.

Synth Commun 2013 ;43(14)

Microbiotix, Inc., One Innovation Drive, Worcester, MA, 01605.

6-Cyanobenzo[]furan-2-boronic acid pinacol ester () is a potentially useful 2-point scaffold for the construction of specific compounds or compound libraries with benzofuran cores. Using a per-iodination/de-iodination strategy coupled with a Sonogashira alkynylation and Cu-catalyzed heteroannulation, we have developed a procedure that allows the preparation of benzo[]furan-6-carbonitrile () and 6-cyanobenzo[]furan-2-boronic acid pinacol ester () in gram quantities. Read More

View Article

Download full-text PDF

Source
http://dx.doi.org/10.1080/00397911.2012.684086DOI Listing
http://www.ncbi.nlm.nih.gov/pmc/articles/PMC3829476PMC
January 2013
12 Reads

SUPERACID-PROMOTED HYDROXYALKYLATION OF 1,2-INDANDIONES.

Synth Commun 2013 ;43(16):2171-2177

Department of Chemistry and Biochemistry, Northern Illinois University, DeKalb, IL 60115.

1,2-Indandione reacts efficiently with arenes to give 2,2-diaryl-1-indanones by the hydroxyalkylation reaction. The Brønsted superacid CFSOH (triflic acid) is an effective catalyst for these condensation reactions. The requisite 1,2-indandiones were prepared from the 1-indanones. Read More

View Article

Download full-text PDF

Source
http://www.tandfonline.com/doi/abs/10.1080/00397911.2012.693
Publisher Site
http://dx.doi.org/10.1080/00397911.2012.693239DOI Listing
http://www.ncbi.nlm.nih.gov/pmc/articles/PMC3797623PMC
January 2013
10 Reads

Esterification Catalysis by Pyridinium -Toluenesulfonate Revisited-Modification with a Lipid Chain for Improved Activities and Selectivities.

Synth Commun 2013 Jan;43(21):2906-2912

Department of Chemistry and Biochemistry, Southern Illinois University, 1245 Lincoln Drive, Carbondale, Illinois 62901-4409.

The lipid analogues of pyridinium -toluenesulfonate (PPTS) were examined for catalyzing the condensation of an equimolar mixture of carboxylic acids and alcohols under mild conditions without removal of water. Although PPTS is a poor catalyst, the introduction of a lipid chain and nitro group significantly improved the activity of PPTS and led to selectivity at suppressing elimination side reactions of alcohols. 2-Oleamido-5-nitro-pyridinium -toluenesulfonate (6) is a lead catalyst that promoted various esterification reactions with yields up to 99%. Read More

View Article

Download full-text PDF

Source
https://www.tandfonline.com/doi/full/10.1080/00397911.2012.7
Publisher Site
http://dx.doi.org/10.1080/00397911.2012.749990DOI Listing
http://www.ncbi.nlm.nih.gov/pmc/articles/PMC3768026PMC
January 2013
12 Reads

THE SYNTHESIS OF C-N-LABELED 3,5-DIIODOTHYRONINE AND THYROXINE.

Synth Commun 2013 5;43(10):1439-1446. Epub 2012 Jun 5.

Department of Physiology and Pharmacology, Oregon Health and Science University, Portland, Oregon, USA.

Thyroid hormones undergo extensive metabolism to regulate hormone activity. A labeled thyroid hormone would be useful to track hormone metabolism through various pathways. While radiolabeled thyroid hormones have been synthesized and used for in vivo studies, a stable isotope labeled form of thyroid hormone is required for studying thyroid hormone metabolism by LC-MS/MS, an analytical technique that has certain advantages without the complications of radioactivity. Read More

View Article

Download full-text PDF

Source
http://dx.doi.org/10.1080/00397911.2011.639005DOI Listing
http://www.ncbi.nlm.nih.gov/pmc/articles/PMC5607869PMC
June 2012
7 Reads

Synthesis of 3-(1-Methyl-1-imidazol-2-ylthio)propanoic Acid and ()-3-(1-Methyl-1-imidazol-2-ylthio)acrylic Acid.

Synth Commun 2013 Jan;43(1):1-8

Mitochondrial Research and Innovation Group, Department of Anesthesiology, and Department of Pharmacology and Physiology, University of Rochester Medical Center, Rochester, NY 14642.

The syntheses of 3-(1-methyl-1-imidazol-2-ylthio)acrylic acid and 3-(1-methyl-1-imidazol-2-ylthio)propanoic acid, mitochondria-targeted prodrugs of the antioxidant methimazole, are described. The method of Fan et al. (Fan et al. Read More

View Article

Download full-text PDF

Source
http://dx.doi.org/10.1080/00397911.2011.587078DOI Listing
http://www.ncbi.nlm.nih.gov/pmc/articles/PMC4036701PMC
January 2013
22 Reads

Cost-effective and Large-scale synthesis of 16:0 Lysophosphatidic Acid.

Synth Commun 2012 Dec 20;42(24):3614-3618. Epub 2012 Aug 20.

University of Virginia, Department of Chemistry, P.O. Box 400319, McCormick Road, Charlottesville, Virginia 22904.

Lysophosphatidic acid (LPA) is a bioactive compound that has gained attention due to its role in neoplastic diseases. Popularity of the compound has necessitated the use of large quantities of the phospholipid for in vivo and in vitro testing but methods for generating LPA require the use costly procedures, namely phosphoramidite coupling reagents. Additionally there has been no reported large-scale synthesis of LPA. Read More

View Article

Download full-text PDF

Source
http://www.ncbi.nlm.nih.gov/pmc/articles/PMC3525677PMC
December 2012
5 Reads

PRACTICAL PREPARATION OF RESVERATROL 3-O-β-D-GLUCURONIDE.

Synth Commun 2012 Jan 20;42(24):3589-3597. Epub 2012 Aug 20.

University of North Dakota, Chemistry Department, 151 Cornell St. Stop 9024, Grand Forks, ND, 58202, USA.

A practical synthesis of resveratrol 3-O-β-D-glucuronide, suitable for preparation of large quantities, was developed using selective deacetylation of resveratrol triacetate with ammonium acetate. A simplified procedure for large scale preparation of resveratrol is also reported. Read More

View Article

Download full-text PDF

Source
http://www.tandfonline.com/doi/abs/10.1080/00397911.2011.585
Publisher Site
http://dx.doi.org/10.1080/00397911.2011.585733DOI Listing
http://www.ncbi.nlm.nih.gov/pmc/articles/PMC3423218PMC
January 2012
11 Reads

SYNTHESIS OF NOVEL BITHIOPHENE-SUBSTITUTED HETEROCYCLES BEARING CARBONITRILE GROUPS.

Synth Commun 2011 Jan;41(3):319-330

Chemistry Department, Faculty of Science, Mansoura University, Mansoura, Egypt.

Symmetrical and unsymmetrical bithiophene-substituted heterocycles bearing carbonitriles including imidazo[1,2-a]pyridine, benzimidazole, and pyridine derivatives have been synthesized via different synthetic protocols. The bithiophene bis-imidazo[1,2-a]pyridine derivatives 3a,b were achieved in three steps starting from 2-acetyl-5-bromothiophene. Suzuki coupling reaction of 2a with 5-formylthiophen-2-ylboronic acid forms the formyl derivative 5, which by condensation with 3,4-diaminobenzonitrile in the presence of sodium bisulfite furnishes the unsymmetrical bithiophene derivative 6. Read More

View Article

Download full-text PDF

Source
http://dx.doi.org/10.1080/00397910903537364DOI Listing
http://www.ncbi.nlm.nih.gov/pmc/articles/PMC3086213PMC
January 2011
6 Reads

Synthesis of Berberine-Efflux Pump Inhibitor Hybrid Antibacterials.

Synth Commun 2010 Jan;40(23):3561-3568

School of Chemistry, University of Wollongong, NSW 2522, Australia.

This paper reports the compact synthesis of two isomeric dual-action hybrid antimicrobials where the 13-position of the antibacterial berberine has been linked via 3'- and 4'-methylene bridges to INF55 (5-nitro-2-phenylindole), an inhibitor of the bacterial NorA multidrug-resistance pump. Read More

View Article

Download full-text PDF

Source
http://dx.doi.org/10.1080/00397910903457415DOI Listing
http://www.ncbi.nlm.nih.gov/pmc/articles/PMC3035389PMC
January 2010
10 Reads

SYNTHESIS OF N-SUBSTITUTED CARBONYLAMINO-1,2,3,6-TETRAHYDROPYRIDINES AS POTENTIAL ANTI-INFLAMMATORY AGENTS.

Synth Commun 2011 29;41(7):2615-2623. Epub 2011 Jun 29.

College of Pharmacy and Pharmaceutical Sciences, Florida A&M University, Tallahassee, Florida, USA.

Several N-substituted carbonyl/sulfonylamino-1,2,3,6-tetrahydropyridines (5a-i and 9a, b) were synthesized via sodium borohydride reduction of the corresponding N-substitutedimino-pyridinium ylides (4a-i and 8a, b) in absolute ethanol. Read More

View Article

Download full-text PDF

Source
http://dx.doi.org/10.1080/00397911.2010.515335DOI Listing
http://www.ncbi.nlm.nih.gov/pmc/articles/PMC3361725PMC
June 2011
12 Reads

A Survey of Solvents for the Conrad-Limpach Synthesis of 4-Hydroxyquinolones.

Synth Commun 2009 Jan;39(9):5193-5196

Microbiotix, Inc. One Innovation Drive Worcester, MA, 01605.

A study on the synthesis of a 4-hydroxyquinoline derivative using the Conrad-Limpach reaction led to the identification of inexpensive and user-friendly solvents for this thermal condensation. Read More

View Article

Download full-text PDF

Source
http://dx.doi.org/10.1080/00397910802542044DOI Listing
http://www.ncbi.nlm.nih.gov/pmc/articles/PMC2744084PMC
January 2009
6 Reads

Synthesis of Chiral Aziridines through Decarboxylative Generation of Sulfur Ylides and their Reaction with Chiral Sulfinyl Imines.

Synth Commun 2009 Jan;39(13):2405-2422

Department of Chemistry, University of South Alabama, Mobile, AL 36688, USA.

Reaction of sulfur ylide with a series of aryl substituted chiral non-racemic sulfinyl imines afforded the corresponding aziridines in high yield and good stereoselection. The sulfur ylides were generated by the thermally induced decarboxylation of carboxymethylsulfonium betaines. A drop in the diastereomeric ratio was observed when going from electron deficient to electron releasing aryl substituted imines. Read More

View Article

Download full-text PDF

Source
http://dx.doi.org/10.1080/00397910802654898DOI Listing
http://www.ncbi.nlm.nih.gov/pmc/articles/PMC2906816PMC
January 2009
31 Reads

Phytochemicals from Echinacea and Hypericum: A Direct Synthesis of Isoligularone.

Synth Commun 2007 Jan;37(8):1251-1257

Department of Chemistry, Iowa State University, Ames, IA 50011.

Reaction of trienes with α,β-unsaturated aldehydes produces bicyclic products via a tandem Diels-Alder/ene reaction. The adduct from tiglic aldehyde was converted into isoligularone by conversion to a furan followed by benzylic oxidation. Read More

View Article

Download full-text PDF

Source
http://www.tandfonline.com/doi/abs/10.1080/00397910701215544
Publisher Site
http://dx.doi.org/10.1080/00397910701215544DOI Listing
http://www.ncbi.nlm.nih.gov/pmc/articles/PMC2000341PMC
January 2007
6 Reads

SYNTHESIS OF SYMMETRICAL METHYLENEBIS(ALKYL HYDROGEN PHOSPHONATES) BY SELECTIVE CLEAVAGE OF METHYLENEBIS(DIALKYL PHOSPHONATES) WITH MORPHOLINE.

Synth Commun 2004 Jan 18;34(2):331-344. Epub 2011 Oct 18.

Department of Chemistry and Biochemistry, MSC 3C, New Mexico State University, Las Cruces, NM 88003.

The preparation of partial esters of methylenebisphosphonic acids has been of recent interest due to their potential therapeutic applications. This paper describes a convenient method to prepare symmetrical methylenebis(alkyl hydrogen phosphonates) by the selective cleavage of the corresponding methylenebis(dialkyl phosphonate) with refluxing morpholine. The effects of structural variations on the amine as well as the substrate have been investigated to understand the scope and limitations of this reaction. Read More

View Article

Download full-text PDF

Source
http://www.tandfonline.com/doi/abs/10.1081/SCC-120027271
Publisher Site
http://dx.doi.org/10.1081/SCC-120027271DOI Listing
http://www.ncbi.nlm.nih.gov/pmc/articles/PMC3505106PMC
January 2004
6 Reads
  • Page 1 of 1