Degradation of ?-Methyl-3,4-dihydroxyphenylalanine (?-MethylDOPA)
H. L. Slates, D. Taub, C. H. Kuo, N. L. Wendler
J. Org. Chem.
1964, 29 (6), pp 1424–1429
DOI: 10.1021/jo01029a039


Abstract
a-MethylDOPA has been degraded in high yield by several pathways to derivatives of 3,4-dihydroxyphenylacetone. These pathways comprise recycle routes for the utilization of D-(+)-a-MethylDOPA in the synthesis of L-(-)-a-MethylDOPA.



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Synthesis of [3-11C]phenylpyruvic acid and its use in an enzymatic transamination to [3-11C]phenylalanine
Christer Halldin & Bengt Längström
Journal of Labelled Compounds and Radiopharmaceuticals
Volume 23(7) 1986 pp.715-722
DOI: 10.1002/jlcr.2580230705


Abstract
The synthesis of [3-11C]phenylpyruvic acid, starting with 11CO2, is reported. This -keto acid was prepared via a condensation reaction, using [11C]benzaldehyde (prepared as described elsewhere), and 2-phenyl-5-oxazolone, using diazabicyclooctane (DABCO) as a base. The condensation product, [-11C]-4-benzylidene-2-phenyl-5-oxazolone, was converted by basic hydrolysis to give [3-11C]phenylpyruvic acid in 40 % radiochemical yield, starting with 11CO2, within 40 min. The potential of [3-11C]phenylpyruvic acid in enzymatic transamination, catalyzed by glutamic/oxaloacetic acid transaminase (GOT) (Ee 2.6.1.1) immobilized on CNBr-activated Sepharose was also studied.

Biotransformation of codeine to morphine in freely suspended cells and immobilized cultures of Spirulina platensis
S. Ramachandra Rao1, Usha Tripathi1 and G.A. Ravishankar
Journal of Microbiology and Biotechnology
1999,Volume 15, Number 4 , pages 465-469
DOI   10.1023/A:1008975901642
                     

Abstract
Both freely suspended cells and immobilized cultures of Spirulina platensis, a blue-green alga, biotransformed exogenously fed codeine, an opium alkaloid, to morphine. The external addition of codeine to the culture medium did not affect the growth of S. platensis. Immobilization of Spirulina in a calcium alginate gel matrix was optimized by using 2% (w/v) sodium alginate and reducing the concentration of nutrients of Zarrouk's medium, which caused destabilization of the calcium alginate gel. The accumulation of morphine increased gradually and reached maxima of 330thinspmgrg 100thinspml–1 culture at 105thinsph in freely suspended and 351thinspmgrg 100thinspml–1 at 96thinsph in immobilized Spirulina cultures. Accumulation of morphine was detected only in the medium, whereas cells did not show accumulation. The immobilized Spirulina cultures showed marginally higher conversion of codeine to morphine over freely suspended cultures.

Synthesis of dimethyl carbonate from urea and methanol over metal oxides
Mouhua Wanga, NingZhaoa, Wei Wei, and Yuhan Sun
Studies in Surface Science and CatalysisVolume 153, 2004, Pages 197-200
DOI: 10.1016/S0167-2991(04)80247-7  


Abstract
A series of metal oxide were used as solid catalysts for synthesis of dimethyl carbonate from urea and methanol. Among them, ZnO was shown to be the highest active catalyst. It was also found that the activity of other oxides such as CaO, MgO, ZrO2 was closely related to their basic strength.

 

Determination of H acidity function for glycolic sodium glycoxide by use of t-butylphenols as indicators and a comparison with that found by use of amine indicators[/u]
Lakshmi Aiyar, Amar Nath Datta and K. K. Kundu
J. Chem. Soc., Perkin Trans. 2,
1972, 1046 - 1050
DOI: 10.1039/P29720001046



Abstract
An H acidity scale, (H)PhEG, for solutions of sodium glycoxide in ethylene glycoxide in ethylene glycol (EG) has been set up at 25 °C by use of t-butylphenols as indicator acids (HA). The value of H in this scale at a particular glycoxide concentration is lower than the corresponding value in the H scale, (H)AmEG, set up earlier for the same system with nitroanilines and -diphenylamines as indicator acids (HA). In a bid to understand the observed differences in the two H values activity coefficients (fHA) of a typical neutral phenol as well as an amine indicator in glycoxide solutions of increasing concentration in glycol (glycol being taken as the standard state) have been determined by solubility and partition experiments respectively. An attempt has been made to explain the observed variation of fHA as a function of glycoxide concentration and to understand the corresponding variation of the activity coefficients of the anions (fA–) of the amine and phenol indicators in these solutions.



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Hammett acidity functions (H–) of lithium, sodium, and potassium glycoxide solutions in ethylene glycol at 25 °C
K. K. Kundu and Lakshmi Aiyar
J. Chem. Soc. B,
1971, 40 - 44
DOI: 10.1039/J29710000040




Abstract
H– scales have been set up for solutions of lithium, sodium, and potassium glycoxides in anhydrous ethylene glycol at 25 °C by use of nitro-substituted anilines and diphenylamines as indicators. The order of increase of H– with alkali concentration is Li < Na < K. This may be due to ion-pair formation which will be in the order Li > Na > K, and is reflected in the H– being in the reverse order, as expected. The H– scales for the three systems (i) NaOH in water, (ii) NaOMe in methanol, and (iii) Na glycoxide in ethylene glycol are compared. A comparison is also made of the aqueous and glycolic systems on a mole-fraction scale, which seems to indicate that, like the autoprotolysis constant, the H– scale in any amphiprotic solvent is largely a composite function of bulk dielectric constant of the solvent, as well as the intrinsic acidity and basicity of the solvent molecules.



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Synthetic Utility and Mechanistic Implications of the Fries Rearrangement of Hydroquinone Diesters in Boron Trifluoride Complexes
Jessica L. Boyer, Jodie E. Krum, Michael C. Myers, Aleem N. Fazal, and Carl T. Wigal
J. Org. Chem.
2000, 65 (15), pp 4712–4714
DOI: 10.1021/jo000412q



Abstract
Reactions of boron trifluoride methyl and ethyl etherate complexes with hydroquinone diesters yield monomethyl and monoethyl derivatives of acetylhydroquinones. The use of sterically hindered boron trifluoride etherate complexes results in acetylhydroquinone derivatives. This procedure represents a one-step synthesis of acetylhydroquinone derivatives, important building blocks for a variety of synthetic applications.



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Analysis of Naphthalenesulfonic Acids and Naphthalene
W. S. Calcott, F. L. English & P. B. Downing
Ind. Eng. Chem.
1924, 16 (11), p 1190
DOI: 10.1021/ie50179a038



Abstract
In a recent paper by the authors upon the "Analysis of Naphthalenesulfonic Acids and Naphthalene," the detailed procedure of analysis and preparation of reagents for the analysis of naphthalenesulfonic acids was accidentally omitted when the article was printed. The methods, which consist in determining the naphthalene carbon present by oxidation of the naphthalene residue to phthalic anhydride, and the sulfonic acid sulfur present by isolation of the soluble barium sulfonates with subsequent gravimetric determinations of barium, are given here.

Synthesis of N-Phthaloyl Derivatives of Amino Acids
S. I. Zav'yalov, O. V. Dorofeeva, E. E. Rumyantseva, L. B. Kulikova, G. I. Ezhova, N. E. Kravchenko and A. G. Zavozin
J.Pharm Chem.
2002,Vol.36(, pp.440-442
DOI: 10.1023/A:1021218828915




Abstract
N-Phthaloyl derivatives of amino acids are used as semiproducts in the synthesis of hypolipidemic [1], analgesic [2], antibacterial [3], and antitumor [4] activity. These N-phthaloyl amino acids (PAAs) are usually synthesized through cyclocondensation of amino acids with phthalic anhydride [5-8]. Some PAAs, representing the N-phthaloyl derivatives (VIII-X) of DL-alanine, B-alanine, and g-aminobutyric acid (GABA), can also be obtained by fusing phthalic acid with the corresponding amino acids (III-V) at 170-190'C[9].
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A two-step method for the preparation of homochiral cathinones
Mauricio Osorio-Olivaresa, Marcos Caroli, Silvia Sepúlveda-Bozab, Bruce K. Casselsc, Ricardo F. Baggiod and Juan C. Muñoz-Acevedo
Tetrahedron: Asymmetry
2003,Volume 14, Issue 11, Pages 1473-1477
DOI: 10.1016/S0957-4166(03)00317-3  

Abstract
A simple method for the preparation of homochiral ring-substituted 1-aryl-2-aminopropanones 2 (‘cathinones’) is described, involving initial Friedel–Crafts acylation of aromatics with (S)- or (R)-N-trifluoroacetylalanyl chloride, followed by acid hydrolysis of the intermediate trifluoroacetamido intermediates 1, for which X-ray diffraction analysis confirmed the structures.

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Enantiomeric .alpha.-aminopropiophenones (cathinone): preparation and investigation
Bertold D. Berrang, Anita H. Lewin and F. Ivy Carroll
J. Org. Chem.
1982, 47 (13), pp 2643–2647
DOI: 10.1021/jo00134a026

Abstract
The preparation of the optical antipodes of a-aminopropiophenone (cathinone) from norephedrine and an improved large-scale resolution of norephedrine are described. The characterization of cathinone and its salts and their stability in various solvents are discussed

Reactions with thioethoxide ion in dimethylformamide. I. Selective demethylation of aryl methyl ethers

GI Feutrill and RN Mirrington
Australian Journal of Chemistry 25( 1719 - 1729
Full text doi:10.1071/CH9721719

Abstract

Recent methods for demethylating aryl methyl ethers have been briefly reviewed, especially methods involving the use of nucleophilic reagents. Sodium thioethoxide dissolved in N,N-dimethylformamide has been developed as a powerful new reagent for demethylating aryl methyl ethers cleanly and rapidly in high yield. The reaction conditions can be controlled so that aromatic bromo substituents or isolated olefinic bonds are unaffected. Of special interest has been the selective monodemethylation of the methyl ethers of di- and tri-hydric phenols, exemplified by the isolation in high yield of orcinol monomethyl ether, p-methoxyphenol, guaiacol, and phloroglucinol dimethyl ether from the respective fully O-methylated compounds. An exception was pyrogallol trimethyl ether which afforded pyrogallol 1-monomethyl ether in high yield.

Synthesis of tryptamines by the Fischer method using synthetic precursors and latent forms of amino-butanal (review)

T. I. Bidylo and M. A. Yurovskaya
Chemistry of Heterocyclic Compounds
Vol.44(4), 2008 pp.379-418
DOI:10.1007/s10593-008-0057-x

Abstract

Information on the synthesis of tryptamines using the Fischer reaction is reviewed. A comparative
analysis is made of the methods of production and the reactivity of the various synthetic precursors and
latent forms of aminobutanal – the carbonyl component in the synthesis of tryptamines by the Fischer
method.

Conclusions in brief
After analysis of existing data on the synthesis of tryptamines using the Fischer reaction it is possible to
reach the following conclusions.
1. Optimum Procedures.
2. Formation of Side Products.
3. Dependence of the Yields on the Structure of the Reagents.

Assessment of the opiate properties of two constituents of a toxic illicit drug mixture.
Johannessen JN, Markey SP.
Drug Alcohol Depend.
1984 Jul;13(4):367-74.



Abstract
The intravenous use of an illicit synthetic drug preparation has caused permanent parkinsonism in a number of addicts. Chemical analysis has revealed the ingredients to be two related compounds 1-methyl-4-phenyl-1,2,3,6-tetrahydropyridine (MPTP) and 1-methyl-4-phenyl-4-propionoxypiperidine (MPPP). The opiate properties of these two compounds have been assessed using in vitro receptor binding techniques as well as behavioral tests indicative of opiate action, including analgesia, catatonia, respiratory depression and the loss of righting and corneal reflexes. All opiate activity was found to reside with MPPP, which proved to be a potent mu-type agonist. It is concluded that the opiate properties of MPPP alone explain repeated abuse of MPTP/MPPP mixtures by heroin addicts.

Characteristics of regeneration of n-methylpyrrolidone
G. A. Rudova and I. Z. Éifer
Fibre Chemistry
1994,Vol.26(2), pp.86-93
DOI:10.1007/BF00551239


Comment by requestee
Without abstract, however, the first page states that N-MP forms salts, which can collected from saturated solutions (or salted out using more soluble salts, ammonium sulfate'll do that), thus avoiding the need to distill the N-MP from the extraneous crud it comes with nowadays.

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The Bücherer-Strecker synthesis of d- and l-(1-11C)tyrosine and the in vivo study of l-(1-11C)tyrosine in human brain using positron emission tomography
Chister Halldin, Karl-Olof Schoeps, Sharon Stone-Elander and Fritz-Axel Wiesel
European Journal of Nuclear Medicine and Molecular Imaging
1987,Vol.13(6),  pp.288-291
DOI: 10.1007/BF00256552



Abstract
The synthesis of d-and l-(1-11C)tyrosine, starting with 11C-cyanide, is reported. dl-(1-11C)Tyrosine was prepared by the Bücherer-Strecker reaction, from carrier added 11C-cyanide with an incorporation of 80% in 20 min. The isolation of the pure d- and l-amino acid isomers from the enantiomeric mixture was accomplished within 15 min by preparative HPLC using a chiral stationary phase and a phosphate buffer as the mobile phase. Typically, the total synthesis time was 50 min (including purification) from end of trapping of 11C-cyanide, with a radiochemical yield of d- and l-amino acid of 40%–60%. The d- and l-(1-11C)tyrosine were both obtained optically pure, with a carrier added specific activity of 0.3–0.5 Ci/mmol and a radiochemical purity better than 99%. The 11C labelled l-tyrosine was used in an in vivo study in the human brain using positron emission tomography (PET).


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Preparation and properties of p-hydroxyphenylacetaldehyde and 3-methoxy-4-hydroxyphenylacetaldehyde
Jay H. Robbins
Archives of Biochemistry and Biophysics
1966, Volume 114(3), pp.576-584
DOI: 10.1016/0003-9861(66)90382-1


Abstract
A simple method for the preparation of the naturally occurring aldehydes, p-hydroxyphenylacetaldehyde and 3-methoxy-4-hydroxyphenylacetaldehyde, is presented. The aldehydes were prepared from synephrine and metanephrine, respectively, by treating the latter compounds with hot acid. The aldehydes were isolated and stored as their stable, crystalline, bisulfite addition products from which they could be conveniently obtained in a highly purified state. Identification of the aldehydes was made by functional group analysis, preparation of suitable derivatives, and by oxidation of the aldehydes to the corresponding acids by xanthine oxidase. Paper chromatography of the aldehydes and other identifying properties are presented.

The synthesis of 14C-safrole, myristicin and elemicin labeled in the allyl side chain
M. Walker, J. McKinney, E. Oswald
Journal of Labelled Compounds
1974, Volume 10(3), Pages 405-411
DOI: 10.1002/jlcr.2590100306



Abstract
The preparation of 1-[ (3-14C)-Allyl]-3,4-methylene dioxy-,1-[(3-14C)-allyl]-3-methoxy-4,5-methylene dioxy-, and 1-[(3-14C)-allyl]-3,4,5-trimethaoxy benzenes is described. The 14C-label was introduced into the 3-carbon of the allylic side chain via the Wittig reaction.



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Iron(III) Chloride as a Lewis Acid in the Friedel-Crafts Acylation Reaction
William H. Miles , Charles F. Nutaitis and Christian A. Anderton
J. Chem. Educ.,
1996, 73 (3), p 272
DOI: 10.1021/ed073p272



Abstract
As one of the most important reactions in aromatic substitution chemistry, the Friedel-Crafts reaction receives extensive coverage in sophomore organic chemistry. The most widely used Lewis acid for the Friedel-Crafts reactiuon is aluminum chloride. The safety and handling problems associated with using aluminum chloride prompted us to examine iron(III) chloride as an alternative Lewis acid for the Friedel-Crafts acylation reaction. In this article we describe an experiment that uses iron(III) chloride. Its use avoids many of the problems commonly associated with aluminum chloride without substantial loss in yield.



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Isolation of oil of clove and separation of eugenol and acetyl eugenol. An instructive experiment for beginning chemistry undergraduates
M. S. Ntamila and A. Hassanali
J. Chem. Educ.,
1976, 53 (4), p 263
DOI: 10.1021/ed053p263



Abstract
The study in this article is simple to perform, requires small quantities of readily available material and may be completed within a normal laboratory period