Author Topic: 2012 Reference Requests (Read 1680 times)

RoidRage · « **Reply #40 on:** March 12, 2012, 01:39:17 AM »

Requested by Assyl Fartrate

Some Spirohydantoins and Ureas Derived from Alkylamino-substituted Alicyclic Ketones
George W. Smith, Allan R. Day
J. Am. Chem. Soc., 1955, 77 (13), pp 3541–3543
DOI: 10.1021/ja01618a034

RoidRage · « **Reply #41 on:** March 12, 2012, 01:41:56 AM »

Requested by no1uno

Clemmensen Reduction of Ketones in Anhydrous Organic Solvents
E. Vedejs
Org. React.
2011 pp.401-422
DOI: 10.1002/0471264180.or022.03

Quote from: no1uno

I'm sure I've seen this cited before, but for some reason when I'm trying to find where the fuck Psychokitty got the procedure (cited here - http://www.erowid.org/archive/rhodium/chemistry/cinnamyl.txt - halfway down the page) for the reduction of cinnamyl chloride to allylbenzene, it keeps coming up. Granted, HCl & Zinc are used in the reaction under discussion, but could it be(e)?

When I search for "Clemmensen Reduction Cinnamyl Alcohol" it keeps coming up with snippets like this:

Quote
...mechanisms involving alcohols as intermediates have been ruled out because alcohols are generally not reduced under Clemmensen condi~ tions.2- 4 ...

or

Quote
Clemmensen Reduction of Ketones in Anhydrous Organic Solvents ...
onlinelibrary.wiley.com › ... › Book Home › Abstract
by E Vedejs - Cited by 49 - Related articles
15 Mar 2011 – The Clemmensen reduction of ketones and aldehydes using zinc and ..... as shown for 3-methylcyclohex-2-enol and cinnamyl alcohol.41 ...
You've visited this page 2 times. Last visit: 23/10/11
Might make for an interesting & highly useful approach if it were true

I found it in the post you initially requested it in may 2011

- RoidRage

RoidRage · « **Reply #42 on:** March 13, 2012, 03:58:04 PM »

Requested by no1uno

Total synthesis of dipiperamide A and revision of stereochemical assignment
Masaki Takahashi, Masaya Ichikawa, Sakae Aoyagi & Chihiro Kibayashi
Tetrahedron Letters
Vol.46(1) 2005 pp.57-59
http://dx.doi.org/10.1016/j.tetlet.2004.11.042

Abstract

The first total synthesis of dipiperamide A has been achieved by employing a solid-state photodimerization of an (E)-cinnamic acid derivative. This critical step results in the cyclobutane ring, which exists in the natural product, with full control of the regio- and stereochemistry at the four stereogenic centers. Results from these studies indicate that the proposed stereostructure of natural dipiperamide A should be revised to the structure originally assigned to dipiperamide B.
[/color]

Development of a Scalable Process for CI-1034, an Endothelin Antagonist
T. E. Jacks, D. T. Belmont, C. A. Briggs, N. M. Horne, G. D. Kanter, G. L. Karrick, J. J. Krikke, R. J. McCabe, J. G. Mustakis, T. N. Nanninga, G. S. Risedorph, R. E. Seamans, R. Skeean, D. D. Winkle and T. M. Zennie
Org. Proc. Res. Dev.
Vol.8(2) 2004 pp 201–212
DOI: 10.1021/op034104g

Abstract

A concise, convergent multikilogram synthesis of CI-1034 (1), a potent endothelin receptor antagonist, is described. A 15-step preparation from commercially available o-vanillin and benzenesulfonyl chloride employs a remarkably robust Suzuki coupling between a boronic acid and an aromatic sulfonate ester as the key synthetic step. A scalable route capable of producing multikilogram quantities of CI-1034 with no chromatographic steps is described in this contribution. Improvements to the process included using a 4-fluorobenzenesulfonate ester as a suitable substitute for the triflate group in the Suzuki reaction and the use of MgCl2 as a substitute for TiCl4 in a Dieckmann condensation to provide the benzothiazine dioxide core.

Additional comments by requestee

Two methylenation articles that might be useful

java · « **Reply #43 on:** March 15, 2012, 01:27:55 AM »

Requested by no1uno

Formation intermediaire de cyclopropanols lors de la reduction de cetones a,ß-ethyleniques dans les conditions de la reaction de clemmensen
Iréne Elphimoff-Felkin & Pierre Sarda
Tetrahedron Letters
1969, Vol.10(35), pp.3045-3048
http://dx.doi.org/10.1016/S0040-4039(01)88340-4

java · « **Reply #44 on:** March 15, 2012, 03:25:03 PM »

requested by Assyl Fartrate

Regio- and Diastereoselective Synthesis of ?-Amino Ketones by Addition of Imines to Iminium Salts†
Dipl.-Chem. Michael Arend,
Prof. Dr. Nikolaus Risch*
Angewandte Chemie International Edition in English
Volume 34, Issue 23-24, pages 2639–2640, January 5, 1996
DOI: 10.1002/anie.199526391

Cannizzaro Reaction of the Cinnamon Aldehyde under Solvent-Free Condition
TIAN Danian,DING Runmei,LIU Wanyi (Ningxia medical college , Yinchuan Ningxia
?DOI?? CNKI:ISSN:1673-5285.0.2007-01-007
http://en.cnki.com.cn/Article_en/CJFDTOTAL-NXSH200701007.htm

java · « **Reply #45 on:** March 15, 2012, 03:29:50 PM »

Requested by no1uno

Reduction par le zinc en presence d'acides—I ?: Reduction des cetones a,ß-ethyleniques avec formation de cyclopropanols
I. Elphimoff-Felkin & P. Sarda
Tetrahedron
Vol.31(22) 1975 pp.2781-2784
http://dx.doi.org/10.1016/0040-4020(75)80289-4

Résumé

La réduction des aryl-2 ou alcoyl-3 cyclohexèn-2 ones substituées 1, 9 et 22, ainsi que celle des arylidène-2 cyclopentanones 2, 14, 16 et 19, par le zinc et l'éther chlorhydrique en présence d'anhydride acétique a fourni des mélanges de produits, constitués essentiellement par des acétates bicycliques et les cétones saturées de même squelette carboné que les cétones initiales.

Abstract

The reduction of 2-aryl or 3-alkyl cyclohex-2-en-ones 1, 9 and 22 and of arylidene cyclopentanones 2, 14, 16 and 19, by zinc and anhydrous HCl in ether in the presence of acetic anhydride, leads to a mixture of bicyclic cyclopropanol acetates and unrearranged saturated ketones[/color]

Reductions par le zinc en presence d'acides—II : Formation de cyclopropanes lors de la reduction des aldehydes aromatiques par le zinc en presence de trifluorure de bore et d'olefines
I. Elphimoff-Felkin & P. Sarda
Tetrahedron
Vol.31(22) 1975 pp.2785-2789
http://dx.doi.org/10.1016/0040-4020(75)80290-0

Résumé

La réduction de plusieurs aldéhydes aromatiques, substitués en para, par le zinc en présence d'éthérate de trifluorure de bore et d'oléfines cycliques ou à chaîne ouverte, d'éthers ou d'acétates vinyliques ou allyliques, fournit les arylcyclopropanes substitués correspondants. Ces résultats témoignent de la formation intermédiaire de carbènes (ou carbénoïdes) dans ces réactions et ouvrent une voie d'accès rapide à de nombreux composés cyclopropaniques.[/color]

Note....comments by requestee,
I got the chem. communications ones on the same topic (and the j.chem.soc one as well). I'll have to get rid of the metadata on another PC before I can add them to this

RoidRage · « **Reply #46 on:** March 19, 2012, 06:03:50 PM »

Requested by Assyl Fartrate

A Convenient Synthetic Method of a 5,7-Diarylcyclopenteno-[1,2-b]pyridine-6-carboxylate: A Key Intermediate for Potent Endothelin Receptor Antagonists
Bioorganic & Medicinal Chemistry
Kenji Niiyama, Takashi Yoshizumi, Hirobumi Takahashi, Akira Naya, Norikazu Ohtake, Takehiro Fukami, Toshiaki Mase, Takashi Hayama, Kiyofumi Ishikawa
Volume 10, Issue 11, November 2002, Pages 3437–3444

RoidRage · « **Reply #47 on:** March 19, 2012, 06:12:40 PM »

Requested by micro

New approach to synthesis of trenbolone
S. N. Pestovskii, S. N. Ananchenko, V. M. Rzheznikov and T. S. Zaitseva
Chemistry of Natural Compounds
Volume 24, Number 2, 263-264,
DOI: 10.1007/BF00596773

M. M. Shemyakin Institute of Bioorganic Chemistry, USSR Academy of Sciences,
Moscow. Translated from Khimiya Prirodnykh Soedinenii, No. 2, pp. 306–307,
March–April, 1988.

java · « **Reply #48 on:** March 22, 2012, 07:16:27 PM »

Requested by micro

IMPROVED METHOD OF SYNTHESIS FOR CLENBUTEROL
Lu Shaorong Wang Fengming
JOURNAL OF GUILIN INSTITUTE OF TECHNOLOGY
1998-01
DOI: cnki:ISSN:1006-544X.0.1998-01-013

java · « **Reply #49 on:** March 22, 2012, 09:12:05 PM »

Requested by Assyl Fartrate

Aspects of stereochemistry. Part III. Metal reduction of some allylic systems
A. S. Hallsworth , H. B. Henbest and T. I. Wrigley
Journal of the Chemical Society (Resumed)
1957, 1969-1974
DOI: 10.1039/JR9570001969

java · « **Reply #50 on:** March 29, 2012, 01:48:59 AM »

Quote from: no1uno on March 21, 2012, 03:46:45 AM

Isolation and structure assignment of an antimicrobial principle from the volatile oil of Nigella sativa L. seeds.

El-Fatatry HM.

Pharmazie.
Vol.30(2) 1975 109-111
PMID: 238225

Abstract

Refrigeration of the volatile oil of Nigella sativa L. seeds eventuates in a crystalline substance. The chemical structure of the compound was drawn from its chemical behaviour, as well as from its UV, IR, PMR and mass spectral data. The compound was found to be thymohydroquinone: confirmation of the structure was established via the preparation of its corresponding diacetate ester. The compound was found to have high antimicrobial effect against gram positive microorganisms.

....this may help, as the study you requested is not available in a digital form.....must be acquired at the stacks in the `university.....java

Chemical composition of Nigella sativa L. seeds
Cevdet Nergiz, Semih Ötle?
Food Chemistry,
1993, Volume 48, Issue 3, Pages 259-261

RoidRage · « **Reply #51 on:** March 29, 2012, 12:45:13 PM »

Requested by fresh1

L-Selectride as a General Reagent for the O-Demethylation and N-Decarbomethoxylation of Opium Alkaloids and Derivatives1
Andrew Coop, James W. Janetka, John W. Lewis, and Kenner C. Rice
The Journal of Organic Chemistry 1998 63 (13), 4392-4396

Direct and Simple O-Demethylation of Thebaine to Oripavine
Andrew Coop, John W. Lewis, and Kenner C. Rice
The Journal of Organic Chemistry 1996 61 (20), 6774-6774

java · « **Reply #52 on:** March 29, 2012, 10:32:46 PM »

Requested by fresh1

Buprenorphine analgesic analogues
United States Patent 5849915

dream0n · « **Reply #53 on:** March 29, 2012, 10:47:45 PM »

Requested by Fresh1

An Improved Method for O-Demethylation of Codeine
J. A. Lawson and J. I. DeGraw
DOI: 10.1021/jm00211a037
Department of Pharmaceutical Chemistry, Stanford Research Institute, Menlo Park, California 94025. Received May 17, 1976

The O-demethylation of codeine was effected by sodium propylmercaptide in dimethylformamide at 125 OC to afford morphine in 80% yield. Similar treatment of thebaine was unrewarding.

java · « **Reply #54 on:** March 30, 2012, 07:04:40 PM »

Requested by no1uno

Expedient Synthesis of Espinatol, p-Methoxycarvacrol and Thymoquinol Dimethyl Ether
Bjora C. Soderberg & Shari L. Fields
Org. Prep & Proc (Int)
Vol.28(2) 1996 pp.221-225
DOI: 10.1080/00304949609356526

java · « **Reply #55 on:** March 30, 2012, 07:14:26 PM »

Requested by fresh1

Lithium chloride-catalyzed selective demethylation of aryl methyl ethers under microwave irradiation
Zhuan Fang,Guo-Chuan Zhou,
Journal of Molecular Catalysis A: Chemical
2007, Volume 274, Issues 1–2, Pages 16–23
http://dx.doi.org.lt.ltag.bibl.liu.se/10.1016/j.molcata.2007.04.013,

java · « **Reply #56 on:** March 31, 2012, 01:56:50 AM »

Requested by Assyl Fartrate

An Efficient One-Pot Synthesis of Unsymmetrical Ethers:? A Directly Reductive Deoxygenation of Esters Using an InBr3/Et3SiH Catalytic System
Norio Sakai,* Toshimitsu Moriya, and Takeo Konakahara
J. Org. Chem.,
2007, 72 (15), pp 5920–5922
DOI: 10.1021/jo070814z

java · « **Reply #57 on:** April 06, 2012, 02:45:08 AM »

Requested by no1uno

On the Condensation of Aldehydes with Ketones. II. Aldehydes with Methylethylketone
Hugh Ryan & Annie Devine
Proceedings of the Royal Irish Academy
Section B: Biological, Geological & Chemical
Vol.32 (1914-1916) pp.208-216
http://www.jstor.org/stable/20490263

Abstract

By condensing benzaldehyde with dimethylacetone Ryan and Dunlea (Proc. Royal. Irish. Acad. xxxiii, B, p.57) obtained a compound obtained a colourless crystalline compound which melted at 168-9C, and which seemed to be the benzylidene derivative of diphenylmethyltetrahydropyrone, the reactions of the compound being best represented by the formula:-

java · « **Reply #58 on:** April 06, 2012, 02:20:11 PM »

Requested by no1uno

The decomposition of daiacl peroxide—IV : Baeyer-Villiger reaction of optically active 3-methyl-4-phenyl-2-butanone
T. Kashiwagi, K. Fujimori, S. Kozuka and S. Oae
Tetrahedron
1970, Vol.26(15), pp.3647-3651
http://dx.doi.org/10.1016/S0040-4020(01)92942-4

Abstract
The stereospecificity of the Baeyer-Villiger reaction of optically active 3-methyl-4-phenyl-2-butanone was investigated. 1-Phenyl-2-propyl acetate was the only oxidation product while the configuration of the original ketone was completely retained in the product.

java · « **Reply #59 on:** April 08, 2012, 03:09:55 PM »

Requested by POSEIDON

Notes- Preparation of 1-Phenyl-2-methyl-2-hydrazinopropane Hydrochloride and Its Isopropyl Derivatives
B Shetty
J. Org. Chem.
1961, 26,8, pp 3002–3004
DOI: 10.1021/jo01066a617

Dihydrobenzofuran Analogues of Hallucinogens. 4.1 Mescaline Derivatives
Aaron P. Monte,† Steve R. Waldman,
J. Med. Chem.
1997, 40 (19), pp 2997–3008
DOI: 10.1021/jm970219x

Author Topic: 2012 Reference Requests (Read 1680 times)

RoidRage

Re: Wanted References and Translations February 2012

RoidRage

Re: Wanted References and Translations February 2012

RoidRage

Re: Wanted References and Translations March 2012

java

Re: Wanted References and Translations March 2012

java

Re: Wanted References and Translations February 2012

java

Re: Wanted References and Translations March 2012

RoidRage

Re: Wanted References and Translations March 2012

RoidRage

Re: Wanted References and Translations March 2012

java

Re: Wanted References and Translations March 2012

java

Re: Wanted References and Translations March 2012

java

Re: Wanted References and Translations March 2012

RoidRage

Re: Wanted References and Translations March 2012

java

Re: Wanted References and Translations March 2012

dream0n

Re: Wanted References and Translations March 2012

java

Re: Wanted References and Translations March 2012

java

Re: Wanted References and Translations March 2012

java

Re: Wanted References and Translations March 2012

java

Re: Wanted References and Translations March 2012

java

Re: Wanted References and Translations March 2012

java

Re: Wanted References and Translations...April 2012