Author Topic: Articles of Interest in Journals and Books  (Read 1495 times)

Naf1

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Re: Articles of Interest in Journals and Books
« Reply #20 on: April 13, 2010, 11:18:23 PM »
Synthetic Preparation of N-Methyl-alpha-amino Acids
Luigi Aurelio, Robert T. C. Brownlee, and Andrew B. Hughes*
Chem. Rev. 2004, 104, 5823-5846

2.1. Nucleophilic Substitution of alpha-Bromo Acids
Fischer and Mechel prepared N-methylalanine, -leucine, and -phenylalanine by nucleophilic displacement of bromide from optically active (R)-R-bromo acids (Scheme 1).
The R-bromo acids were nucleophilically substituted with excess methylamine at 0 °C, providing NMAs with opposite configuration to the parent amino acids. In this mode, they prepared N-methylalanine, -leucine, and -phenylalanine, all of the L-configuration (Scheme 1).

          


http://127.0.0.1/Naf1/2009531202642_n-methylation.aminoacid.pdf
« Last Edit: April 13, 2010, 11:20:25 PM by Naf1 »

java

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Re: Articles of Interest in Journals and Books
« Reply #21 on: July 01, 2010, 12:03:23 AM »
It's almost luck running into some gems now and then while looking for something else,....i found the following patent quite interesting
feel it has merits , ......ofcourse this may be old news, but new to me, so i thought i say so.......java

Process of Preparing 1-phenyl -2-aminopropane  
Shinohara, Tamura. Hosoda
US Patent 3193581





« Last Edit: July 01, 2010, 12:04:55 AM by java »
¡Prefiero morir de pie que vivir siempre arrodillado!.Emiliano ZapataIt is better to die on your feet than to live on your knees!.......

Naf1

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Re: Articles of Interest in Journals and Books
« Reply #22 on: July 22, 2010, 03:13:47 AM »
Analytical characterisation of the routes by thermolytic decarboxylation from tryptophan to tryptamine using ketone catalysts, resulting in tetrahydro-b-carboline formation
Simon D. Brandt a, David Mansell b, Sally Freeman b, Ian A. Fleet c, John F. Alder
Journal of Pharmaceutical and Biomedical Analysis 41 (2006) 872–882

Abstract
N-Alkylated tryptamines have complex psychoactive properties. Routes for clandestine synthesis are described on Internet websites one of which involves the thermolytic decarboxylation of tryptophan to tryptamine as a precursor to psychoactive compounds. High boiling solvents and ketone catalysts have been employed to facilitate the decarboxylation of tryptophan. The present study has revealed that there is formation of tetrahydro-b-carboline (THBC) derivatives which may originate from reaction with both the solvent and the ketone catalyst. The application of gas chromatography electron- and chemical-ionisation ion trap tandem mass spectrometry (GC–IT-MS–MS), in combination with nuclear magnetic resonance (NMR), led to the isolation and identification of 1,1-disubstituted-tetrahydro-b-carbolines formed as major impurities in the tryptamine. Confirmation was by synthesis of the THBC derivatives from tryptamine using Pictet-Spengler cyclisation. Under EI-conditions, mass spectral characterisation of the THBCs suggests predominance of alkyl cleavage

http://wiki.dmt-nexus.com/w/images/a/ab/JPharmBioAn-41-3-872.pdf

embezzler

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Re: Articles of Interest in Journals and Books
« Reply #23 on: July 24, 2010, 10:06:03 PM »
@ Tasthoggua

Here are the pages from that mycology book we discussed. Nice diagrams for the claviceps lifecycle. Note the date of publication is 1952 but its interesting anyway.

Hope im not hijacking the thread too much
All that we see or seem is but a dream within a dream...

Sedit

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Re: Articles of Interest in Journals and Books
« Reply #24 on: August 15, 2010, 01:41:56 AM »
0-Methylation  of  Catechol  Amines  in  Viva*
JULIUS  AXELROD,
SIRO  SENOH,  AND  BERNHARD  WITKOP

From  the  National  Institute  of  Mental  Health  and  the  National  Institute  of  Arthritis  and  Metabolic  Diseases,  United States  Public  Health  Service, Bethesda, Maryland


Although  the  metabolism  of  catechol  amines,  such  as  epi-
nephrine,  norepinephrine,  and  3-hydroxytyramine  (dopamine)
was  thought  at  one  time  to  proceed  mainly  by  deamination
,  the  possibility  of other  pathways  has  been  recognized.

Recently,  Armstrong  and  McMillan   have  found  3-methoxy-
4hydroxymandelic  acid  to  be a  major  metabolite  of  epineph-
rine  and  norepinephrine.  Three  possible  pathways  are  sug-
gested  by  these  findings:  deamination  of  amines  is  followed
by  0-methylation;  0-methylation  precedes  deamination;
 both  pathways  operate  concurrently.  The  following  study
demonstrates  the  normal  occurrence  of  O-methyl  metabolites
of  catechol  amines  in  urine  and  certain  tissues  as  well  as  the  O-
methylation  of  administered  catechol  amines.  These  naturally
occurring  derivatives  of  epinephrine  and  norepinephrine  which
have  a methyl  ether  group  on  the  phenolic  hydroxyl  in  a  position
meta  to  the  side  chain,  will  be  called  metanephrine  and  normeta-
nephrine.
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Bluebottle

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Re: Articles of Interest in Journals and Books
« Reply #25 on: September 08, 2010, 06:06:43 PM »
Addition of heterocycles to electron deficient olefins and alkynes catalyzed by gold(III)
Zigang Li, Zhangjie Shi, Chuan He
Journal of Organometallic Chemistry
2005,Volume 690, Issue 23,  Pages 5049-5054
doi:10.1016/j.jorganchem.2005.03.009


Abstract
A gold(III)-catalyzed hydroarylation of different olefins is reported here. AuCl3 works as an excellent catalyst to mediate reactions between various heterocycles and electron deficient olefins and alkynes under mild conditions. This gold(III)-based method tolerates different functional groups such as aldehyde, carboxylic acid, nitrile, and is highly efficient. We have shown that some of these reactions complete in minutes at room temperature.


[edit] Very interesting take a look, possibly relevant to indoles and JWH. And maybe even 2C/DOX.

« Last Edit: September 13, 2010, 11:36:27 AM by java »
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Enkidu

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Re: Articles of Interest in Journals and Books
« Reply #26 on: December 17, 2010, 11:08:47 AM »
Lewis acid induced rearrangement of 2,3-epoxy sulfides; regiospecific trapping of thiiranium ion intermediates with nitrogen heterocycles and amides. Use of imines as nucleophilic equivalents for the selective monoalkylation of primary amines
Duncan M. Gill, Neil A. Pegg and Christopher M. Rayner
Tetrahedron Volume 52, Issue 10, 4 March 1996, Pages 3609-3630 doi:10.1016/0040-4020(96)00036-1

Quote
The Lewis acid induced conversion of 2,3-epoxy sulfides into the corresponding 3-trimethylsilyloxy-1,2-thiiranium ions is described. Such intermediates react with silylated nitrogen heterocycles and amides regiospecifically to form 1-substituted-3-hydroxy-2-thioethers in good to moderate yields with full stereochemical control. Exclusive N-alkylation is observed. When simple primary amines are used as nucleophiles, only products of polyalkylation are isolated. However, imines can be effectively used as the nucleophilic equivalent of a primary amine, the initially formed iminium ions being readily hydrolysed by aqueous base to liberate a secondary amine, the product of overall selective monoalkylation of a primary amine.

Enkidu

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Re: Articles of Interest in Journals and Books
« Reply #27 on: January 13, 2011, 10:07:45 PM »
THE SEARCH FOR MORPHINE SUBSTITUTES
Dodds
British medical bulletin 4(2) pp.88-91 1946

tag: alpha,beta-diphenylethylamine

Bluebottle

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Re: Articles of Interest in Journals and Books
« Reply #28 on: January 19, 2011, 11:00:20 PM »
The Reaction of Organoboranes with Chloramine and with Hydroxylamine-O-sulfonic Acid. A Convenient Synthesis of Amines from Olefins via Hydroboration

Herbert C. Brown, Wolfgang R. Heydkamp, Eli. Breuer, William S. Murphy
J. Am. Chem. Soc., 1964, 86 (17), pp 3565–3566
DOI: 10.1021/ja01071a036
Publication Date: September 1964

You may have all seen this by now, but in case you haven't. I know how much y'all like those amines.  :P
"And now we divide both sides by zero..."

Bluebottle

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Re: Articles of Interest in Journals and Books
« Reply #29 on: March 07, 2011, 03:46:58 AM »
Preparation of Alkyl Carbamate of 1-Protected Indole-3-methylamine as a Precursor of Indole-3-methylamine

In which they perform a Hofmann rearrangement on 1-protected indoles in incredible yield, using iodobenene diacetate as the oxidant.

Note:   I couldn't find too many accessible 1-acylations for indole; acetic anhydride with catalytic sodium acetate gives a 60% yield according to Studies on Acetylation of Indoles, MOHAMED N IBRAHIM . I thought I had saw a description for 1-acylation of indoles using acyl chloride and KF/Al2O3 as the catalyst/base but I could find it nowhere! Please post it or direct me to it if you have it.




3-Indolepropionic Acid
HERBERT E. JOHNSON AND DONALD G. CROSBY

"3-Indolepropionic acid has been prepared in 56% yield by the reaction of indole with acrylic acid in the presence of acetic anhydride... a-Acetamidoacrylic acid, however, reacts with indole in the presence of acetic anhydride to give acetyltryptophan."




3-Indolepropionic Acid. Some Reactions of Indole with Salts of Acrylic and Methacrylic Acids
HERBERT E. JOHNSON AND DONALD G. CROSBY

"Indole and sodium acrylate react at 250 deg. to give high yields of 3-indolepropionic acid. Methacrylate salts react similarly. The probable mechanism, origin of by-products, and limitations of this novel reaction are discussed."

Note: There is a patent for precipitating the indole-3-propionate as its calcium salt on formation, evidently being much less soluble.



« Last Edit: March 07, 2011, 03:52:45 AM by Bluebottle »
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jon

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reductive amination using borane, borohydrides and, cyanoborohydrides
« Reply #30 on: March 10, 2011, 04:06:26 AM »
this book is gold for you out there interested in things like 'the cold method'
and reductive aminations using these reagents
« Last Edit: March 10, 2011, 02:35:06 PM by java »

lugh

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Re: reductive amination using borane, borohydrides and, cyanoborohydrides
« Reply #31 on: March 10, 2011, 04:59:34 AM »
That's Organic Reactions 59 (2002)  8)
Chemistry is our Covalent Bond

2bfrank

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Re: Articles of Interest in Journals and Books
« Reply #32 on: April 02, 2011, 12:25:56 PM »
Hydroboration Characteristics of Lithium
Borohydride/Ethyl Acetate in Ethyl Ether. A New System for Controlled
Hydroboration of Alkenes and Alkynes’

Facile Reduction of Carboxylic Acids by
Zinc Borohydride

2bfrank

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Re: Articles of Interest in Journals and Books
« Reply #33 on: April 06, 2011, 04:10:41 AM »
EVALUATION OF COLUMN EXTRACTION: A NEW(Not quite- 1976) PROCEDURE FOR
THE ANALYSIS OF DRUGS IN BODY FLUIDS, (as well as aquarious solutions
specifically made.)


Principles of column extraction
An aqueous sample, such as urine, serum or blood, or aquarous solution of various
types is applied to and
absorbed by, a column packed with granular support material, and remains
on the column as the stationary phase. The column is then eluted with
organic, water-immiscible solvents (Fig. 1).
This causes lipophilic compounds such as drugs and their metabolites, to
become extracted from the aqueous phase into the solvent, so that they are
obtained in the eluate. The latter is free of emulsions. The eluate can either
be tested directly or evaporated down to a residue in which the substances
are then determined in concentrated form. It is not necessary to dry the
solution prior to evaporation.
Columns are prepared from 50 ml plastic syringes, filled with 70 ml of
granular diatomaceous earth (Extrelut@, E. Merck, Darmstadt). The
solvent flow is regulated by steel needles connected with the syringe outlet.
20 ml of the aqueous solution is applied onto the column and absorbed
by the support. After 10 minutes the column is eluted with organic
solvent - for urine samples 40 ml of solvent yield a total of 25 ml of eluate
within 5 to 15 minutes.

Now of course this is not limited to bodily fluids. This could be extremely advantageous to a myriad of
extraction requirements.
Also the pH of a solution may be changed on the column. So
the subsequent extraction of drugs from acid and alkaline media can be
performed on the column (Table I). The neutralization of the urine after acid
elution is achieved by drawing ammonia through the column, rendering the
pH of the absorbed solution from 2 to 10.
Basically, all soluents which are employed in liquid-liquid extractions may
be used for column extraction; for instance ether, ethyl acetate, chloroform,
or alcoholic mixtures such as a mixture of dichloromethane/isopropanol
(85:15).
« Last Edit: April 06, 2011, 04:20:36 AM by ziggy »

akcom

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Re: Articles of Interest in Journals and Books
« Reply #34 on: April 06, 2011, 04:40:47 PM »
Gradients columns (pH, solvent, or whatever) are a bit of a pain in the ass.  Did you have any specific use in mind for this stuff?  Without a air compressor this sort of technique takes for ever.  Plus solvent volumes really make it a non starter unless you have A LOT of free time or a rotovap

aniracetam

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Moths that Vector a Plant Pathogen also Transport Endophytic Fungi and Mycoparas
« Reply #35 on: April 16, 2011, 06:48:34 PM »
Feldman et al. (2008)
Microb. Ecol. 56:742–750
« Last Edit: April 16, 2011, 07:01:06 PM by aniracetam »
"Experiments are the only means of knowledge at our disposal. The rest is poetry, imagination." - Max Planck

Enkidu

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Re: Articles of Interest in Journals and Books
« Reply #36 on: May 12, 2011, 12:12:54 AM »
Recent advances in the application of bromodimethylsulfonium bromide (BDMS) in organic synthesis
Lokman H. Choudhury, Tasneem Parvin, and Abu T. Khan
Tetrahedron Volume 65, Issue 46, 14 November 2009, Pages 9513-9526 doi:10.1016/j.tet.2009.07.052

Baba_McKensey

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Re: Translation of articles request Thread
« Reply #37 on: June 09, 2011, 10:10:32 PM »
I found these using google.

The Oxidation of 3-Aryl-1-propenes by Oxidative System of RuCl3-NaIO4-Phase Transfer Catalyst
 Synthetic Communications: An International Journal for Rapid Communication of Synthetic Organic Chemistry
 Volume 33,  Issue 22,  2003, Pages 3947 - 3952
Authors: Yoshifumi Yuasaa; Shiroshi Shibuyab; Yoko Yuasab
http://www.informaworld.com/smpp/ftinterface~content=a713940851~fulltext=713240930~frm=content

ozonation of gama-asarone
http://www.publish.csiro.au/?act=view_file&file_id=CH9683001.pdf

Love Drugs 2005 - Otto Snow
Results 54 - 75 ... Ber., 41, 4148 (1908). 5. Ber., 39: 2933 (1906). ...... Source: Source 1934 Phenylacetaldehyde from Phenylglycidic acid or ester by Wilfred William Groves ..... of which safrole, myristicin and elemicin were identified. ...... Example 2 Ozone having a concentration of 5—8% is led into a well stirred ...
www.scribd.com/doc/44381376/Love-Drugs-2005-Otto-Snow

Sedit

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Re: Articles of Interest in Journals and Books
« Reply #38 on: June 10, 2011, 04:48:03 AM »
My computer is fritzing out again,To much internet smut I assume, so I better post these since im not done reading them for safe keeping.
There once were some bees and you took all there stuff!
You pissed off the wasp now enough is enough!!!

Enkidu

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Re: Articles of Interest in Journals and Books
« Reply #39 on: June 16, 2011, 06:19:05 AM »
Readily Made Solvated Electrons
Jorge G. Ibanez, Francisco J. Guerra-Millan, Muhamad Hugerat, Jorge L. Vazquez-Olavarrieta, Ahmad Basheer, and Riam Abu-Much
J. Chem. Educ., 2011, 88 (5), pp 670–672 DOI: 10.1021/ed100179d
Quote
The existence of solvated electrons has been known for a long time. Key methods for their production (i.e., photoionization of reducing ions, water radiolysis, and the reaction between H· and OH?) are unsuitable for most school laboratories. We describe a simple experiment to produce liquid ammonia and solvated electrons using materials commonly available, without the dangers associated with the use of solid Na or K metal.


NICE - added another article on the preparation of anhydrous ammonia (which describes drying it using nothing more than flask/tube cooled to well below 0C in the train). Anyone got access to the article on the extraction of Li metal from the battery (final reference)
« Last Edit: June 17, 2011, 04:14:41 AM by no1uno »