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Abstract
Graphical Abstract Section
Abstract
Synth. Commun. 2006, 35, 259
NOVEL SYNTHESIS OF OPTICALLY ACTIVE 2‐ETHYLHEXANOIC ACID, 2‐ETHYLHEXANOL, AND 2‐ETHYLHEXYLAMINE VIA THE ASYMMETRIC FAVORSKII REARRANGEMENT
Motofumi Miura, Masaharu Toriyama, and Shigeyasu Motohashi
College of Pharmacy, Nihon University, Chiba, Japan
Abstract
Synth. Commun. 2006, 35, 265
ONE‐POT SUBSTITUTION‐REARRANGEMENT REACTION OF 2‐CHLOROGLYCIDIC ESTER: EFFECTIVE PROTOCOL FOR THE PREPARATION OF 3‐ARYLSULFENYL‐2‐KETO ESTER
Takuzo Komiyama, Yutaka Takaguchi, and Sadao Tsuboi
Department of Material and Energy Science, The Graduate School of Environmental Science, Okayama University, Okayama, Japan
Abstract
Synth. Commun. 2006, 35, 271
FAST SYNTHESIS OF SUBSTITUTED N‐PHENYLANTHRANILIC ACIDS USING ULLMANN CONDENSATION UNDER MICROWAVE IRRADIATION IN DRY MEDIA
Ana Martín, Miriam Mesa, Maite L. Docampo, Victoria Gómez, and Rolando F. Pellón
Center of Pharmaceutical Chemistry, Havana, Cuba
Substituted N‐phenylanthranilic acids using the Ullmann condensation under microwave irradiation in dry media were obtained in good yield and short reaction times.
Abstract
Synth. Commun. 2006, 35, 279
SYNTHESIS OF 4‐SUBSTITUTED PIPERIDINES VIA A MILD AND SCALABLE TWO‐STEP CU2O‐MEDIATED DECARBOXYLATION OF CYANOESTERS
Brian A. Chauder,1 Eric E. Boros,1 Kien S. Du,1 Wieslaw M. Kazmierski,1 Cecilia S. Koble,1 James B. Thompson,1 and Elie A. Tabet2
1Metabolic and Viral CEDD Chemistry, GlaxoSmithKline, Five Moore Drive, Research Triangle Park, North Cardina, USA
2Chemical Development, GlaxoSmithKline, Five Moore Drive, Research Triangle Park, NC, USA
Abstract
Synth. Commun. 2006, 35, 285
CONVENIENT METHOD FOR THE 3‐FUNCTIONALIZATION ISOINDAZOLES
Aaron Bunnell, Counde O'Yang, Andra Petrica, and Michael J. Soth
Department of Medicinal Chemistry, Roche Palo Alto LLC, Palo Alto, California, USA
The C‐3 position of isoindazoles is readily functionalized by metalation with lithium diisopropylamide followed by reaction with a variety of electrophiles.
Abstract
Synth. Commun. 2006, 35, 295
PREPARATION OF PRIMARY THIOAMIDES FROM NITRILES USING SODIUM HYDROGEN SULFIDE AND DIETHYLAMINE HYDROCHLORIDE
Mark L. Boys and Victoria L. Downs
Department of Chemistry, Pfizer Global R&D, Ann Arbor, Michigan, USA
Abstract
Synth. Commun. 2006, 35, 299
ECONOMICAL AND CONVENIENT CARBONYL TRANSPOSITION APPROACH TOWARDS A 2‐ARYLCYCLOHEPTANONE DERIVATIVE
Andrea B. J. Bracca and Teodoro S. Kaufman
Instituto de Química Orgánica de Síntesis (IQUIOS), Universidad Nacional de Rosario, Rosario, Argentina
A convenient, straightforward, and easy access to 2(2,3‐dimethoxyphenyl)cycloheptanone, which employs an heteroatom‐facilitated ortho‐lithiation coupled to a carbonyl transposition strategy, is reported. The synthetic approach avoids using very expensive reagents or difficult‐to‐prepare starting materials.
Abstract
Synth. Commun. 2006, 35, 311
NEW ACCESS TO SESQUITERPENE HYDROQUINONES: SYNTHESIS OF (+)‐ENT‐CHROMAZONAROL
José Villamizar,1 Federico Plata,1 Nieves Canudas,2 Eleonora Tropper,1 Juan Fuentes2 and Angel Orcajo1
1Centro de Química, Instituto Venezolano de Investigaciones Científicas (I.V.I.C.), Caracas, Venezuela
2Departamento de Química, Universidad Simón Bolívar, Valle de Sartenejas, Caracas, Venezuela
A facile access to optically active ( + )‐ent‐chromazonarol ent‐1, isolated from the sponge Disidea pallescens, is reported from commercially available ( + )‐manool 4.
Abstract
Synth. Commun. 2006, 35, 321
MICROWAVE‐ASSISTED BECKMANN REARRANGEMENT: CONVENIENT SYNTHESIS OF 1,3‐DIAZA‐BICYCLO[3.2.2]NONANE
Michael P. Curtis, William H. Bunnelle, Thomas G. Pagano, Murali Gopalakrishnan, and Ramin Faghih
Neuroscience Reasearch, Global Pharmaceutical Research and Development, Abbott Laboratories, Abbott Park, Illinois, USA
A convenient synthesis of 1,3‐diaza‐bicyclo[3.2.2]nonane using microwave irradiation was achieved.
Abstract
Synth. Commun. 2006, 35, 327
EFFICIENT PREPARATION OF HYBRID LINEAR‐BRANCHED ESTERS OF PEG‐PEE DERIVATIVES
Alexander Fishman, Austin Acton, and Edward Lee‐Ruff
Department of Chemistry, York University, Toronto, Ontario, Canada
A simple and efficient preparation of a number of hybrid linear‐branched PEG esters are described. The polymers are generated by direct coupling of PEG–carboxylic acids and a variety of pentaerythritol ethoxylates using carbon tetrabromide catalyst.
Abstract
Synth. Commun. 2006, 35, 331
BROMINATION PRODUCTS OF 2‐SUBSTITUTED 5,7‐DIMETHOXY‐4‐NAPHTHOLS
Ivan R. Green,1 Victor I. Hugo,2 and Mawonga N. Mei1
1Department of Chemistry, University of the Western Cape, Bellville, South Africa
2Department of Chemistry, Cape Peninsula University of Technology, Cape Town, South Africa
The influence of the R1 group of 13 and 21 on the major products 14 and 24 of bromination are described.
Abstract
Synth. Commun. 2006, 35, 347
EFFICIENT PREPARATION OF ((3‐CHLORO‐2‐FLUORO‐PHENYL)‐[7‐METHOXY‐8‐(3‐MORPHOLIN‐4‐YL‐PROPOXY)‐10,11‐DIHYDRO‐5‐OXA‐2,4,11‐TRIAZA‐DIBENZO(A,D)CYCLOHEPTEN‐1‐YL]‐AMINE) FOR IN‐VIVO STUDY
Hu Liu, Leon M. Smith II, Yunyu Mao, Weitao Pan, Yong‐Jiang Xu, Sabina Burdzovic‐Wizeman, Matthew A. J. Duncton, and Wai C. Wong
Department of Chemistry, ImClone Systems Incorporated, Brooklyn, New York, USA
An improved route for the preparation of highly functionalized 5,6‐dihydro‐pyrimido[4,5‐b][1,4]oxazepine 1a in multigram quantities was developed. This new methodology was highlighted by the proper methoxy disposition via a regioselective methylation of 2,4,5‐trihydroxy‐benzaldehyde followed by a magnesium sulfate–promoted cyclization.
Abstract
Synth. Commun. 2006, 35, 355
SYNTHESIS OF TETRAHYDOBENZAZEPINESULFONAMIDES AND THEIR REARANGEMENT TO DIARYLSULFONES
Hui Ren, Murray Zanger, and James R. McKee
Department of Chemistry & Biochemistry, University of the Sciences in Philadelphia, Philadelphia, PA, USA
The acid‐catalyzed rearrangement of benzodiazepinesulfonamides is used to prepare a new class of diarylsulfones, which may have anti‐HIV activity.
Abstract
Synth. Commun. 2006, 35, 365
SYNTHESES OF PANTOLACTONE AND PANTOTHENIC ACID DERIVATIVES AS POTENTIAL LIPID REGULATING AGENTS
Daniela C. Oniciu,1 Roel P. L. Bell,2 Bruce H. McCosar,3 Charles L. Bisgaier,1 Jean‐Louis H. Dasseux,1 Dennis Verdijk,2 Mike Relou,2 Dennis Smith,2 Henk Regeling,2 Frank M. C. Leemhuis,2 Eelco J. Ebbers,2 Ralf Mueller,3 Lian Hao Zhang,3 Emil Pop,3 Clay T. Cramer,1 Brian Goetz,1 Andrew McKee,3 Michael E. Pape,1 and Brian R. Krause1
1Esperion Therapeutics, Pfizer Global Research and Development, Ann Arbor, Michigan, USA
2MercaChem BV, Nijmegen, The Netherlands
3Alchem Laboratories Corporation, Alachua, Florida, USA
Abstract
Synth. Commun. 2006, 35, 393
CONDITION‐DIRECTABLE REACTION: REGIO‐ AND STEREOSELECTIVE ELIMINATION OF 2,3‐DIBROMO‐2‐METHYLPROPYL PHENYL SULFONE VIA BASE‐SOLVENT SELECTION
Xiaojin Li
Laboratory of Immunogenetics, National Institute of Allergy and Infectious Diseases, National Institutes of Health, Rockville, Maryland, USA
Abstract
Synth. Commun. 2006, 35, 401
SYNTHESIS OF HOMOALLYLIC ALCOHOLS FROM KETONES IN WATER
Jun Wang and Gu Yuan
Key Laboratory of Bioorganic Chemistry and Molecular Engineering of Ministry of Education, Department of Chemical Biology, College of Chemistry, Peking University, Beijing, China
Homoallylic alcohols have been prepared in good yields by allylation of ketones with allyl bromide in the presence of stannous chloride dihydrate, zinc iodide, and ammonium chloride in water.
