Graphical Abstracts

Abstract

Synth. Commun. 2003, 33, 2181

Surface-Mediated Hydrohalogenation of Isoprene: A Facile Preparation of Prenyl Halides

Marcio C. S. de Mattos^1,* and Antonio Manzolillo Sanseverino²

¹Instituto de Química, Departamento de Química Orgânica, and ²Escola de Ciências Biológicas, Departamentos de Ciências Naturais, Universidade Federal do Rio de Janeiro, Caixa Postal 68545, 21949-90, Rio de Janeiro, Brazil.

Abstract

Synth. Commun. 2003, 33, 2187

Solvent Effect in the Wittig Reaction under Boden's Conditions

Enrique M. Pandolfi,* Gloria V. López, Eduardo Días, and Gustavo A. Seoane

Departamento de Química Orgánica, Facultad de Química, Av. Gral. Flores 2124, 11800, Universidad de la República, Montevideo, Uruguay

An interesting change in the stereochemical outcome of the Wittig olefination reaction under Boden's conditions (potassium bases and 18-crown-6 as the ylide forming reagent) is reported. This effect depends significantly on the polarity of the solvents and the nature of the ylide.

Abstract

Synth. Commun. 2003, 33, 2197

Highly Diastereoselective Alkylation of the Dellaria Oxazinone Template with Bifunctional Electrophiles

Gregory H. P. Roos^1,* and Kim A. Dastlik²

¹Chemistry Department, Sultan Qaboos University, Sultanate of Oman

²Chemistry Department, Murdoch University, Perth, Western Australia

This study investigates the efficiency of alkylation of the Dellaria oxazinone glycinate template with sensitive bifunctional electrophiles. In addition to improved access to the template, triflate/halide bifunctional combinations provided good yields (85–93%) of highly diastereoselective alkylation products.

Abstract

Synth. Commun. 2003, 33, 2209

Alkynylation of 4- Bromo - 3- Phenylsydnone with Aryl Acetylenes

Kenneth Turnbull,* Douglas M. Krein, and Scott A. Tullis

Chemistry Department, Wright State University, Dayton, Ohio 45435, USA

Various 4-arylethynyl sydnones 2 can be prepared in good yields by reaction of 4-bromo-3-phenylsydnone (1) with aryl acetylenes under palladium catalysis.

Abstract

Synth. Commun. 2003, 33, 2215

The Synthesis of Novel Cis-α-Substituted-β-Aminotetralins

Mark A. Youngman, Nicole M. Willard, Scott L. Dax, and James J. McNally*

Johnson & Johnson Pharmaceutical Research and Development, LLC, Welsh and McKean Roads, Spring House, PA 19477, USA

Teteralones were converted, in 1 to 3 steps, to α-substituted tetralones. Subsequent reductive amination with ammonium acetate/sodium cyanoborohydride gave the corresponding α-substituted-β-aminotetralins, on a multi gram scale, with minimal chromatographic purification for the entire transformation.

Abstract

Synth. Commun. 2003, 33, 2229

A Simple two-Step Synthesis of Indoles

Andrew Walkington,* Matthew Gray, Frank Hossner, John Kitteringham, and Martyn Voyle

Synthetic Chemistry Department, GlaxoSmithKline, New Frontiers Science Park, Harlow, Essex, UK

A two-step synthesis of indoles that is suitable for use on a large scale is described. The general applicability of this methodology has also been briefly explored.

Abstract

Synth. Commun. 2003, 33, 2235

Potassium Cyanate as an Amino-Dehydroxylating Agent: Synthesis of Aminooxypyrrole Mono, Dicarboxylic Acid Esters, and Carbonitrile

Fabrice Jourdan,^1,* Jens T. Kaiser,² and David J. Lowe¹

¹John Innes Centre, Department of Biological Chemistry, Colney, Norwich, NR4 7UH, UK

²Max Planck Institut für Biochemie, AM Klopferspitz 18a, D-82152 Martinsried, Germany

Abstract

Synth. Commun. 2003, 33, 2243

A New Class of Dihydropyridine Thioglycosides via Piperidinium Salts

Adel M. Attia¹ and Galal H. Elgemeie^2,*

¹Department of Chemistry, Faculty of Education, Kafr El-Sheikh, Egypt

²Department of Chemistry, Faculty of Science, Helwan University, Ain-Helwan, Cairo, Egypt

A first reported method for preparation of a new class of thioglycosides via reaction of piperidinium salts of dihydropyridinethiones with 2,3,4,6-tetra-O-acetyl-α-d-gluco and galactopyranosyl bromides has been studied. Comparison with the products obtained from silylated thiopyridines is made.

Abstract

Synth. Commun. 2003, 33, 2257

Microwave-Assisted Coupling of Carboxylic Acids to a Polymer Bound Hydrazine Linker

Charlotta Lindquist,¹ Ulf Tedebark,² Oguz Ersoy,^2,* and Peter Somfai^1,*

¹Organic Chemistry, Department of Chemistry, Royal Institute of Technology, S-100 44 Stockholm, Sweden

²Amersham Biosciences, S-751 84 Uppsala, Sweden

Abstract

Synth. Commun. 2003, 33, 2263

The Anion of 3-Methyl-2-Pyridin-4-YL-1,3-Oxazine

Peter Sheldrake,^1,* Elizabeth Tyrrell,^2,* Shirin Mintias,² and Imran Shahid²

¹Department of Synthetic Chemistry, GlaxoSmithKline Pharmaceuticals, Old Powder Mills Nr. Leigh, Tonbridge, TN11 9AN, UK

²School of Chemical and Pharmaceutical Sciences, Kingston University, Penrhyn Road, Kingston, KT1 2EE, UK

Abstract

Synth. Commun. 2003, 33, 2269

Electrochemical Sulfonylation of 4-Tert-Butylcatechol

Davood Nematollahi,* Ramazanali Rahchamani, and Maryam Malekzadeh

Department of Chemistry, Faculty of Science, University of Bu-Ali-Sina, Hamadan, Iran

Abstract

Synth. Commun. 2003, 33, 2275

A New way to Tert-Butyl [(4R,6R)-6-Aminoethyl-2,2-Dimethyl-1,3-Dioxan-4-yl]Acetate, A Key Intermediate of Atorvastatin Synthesis

Stanislav Rádl*

Research Institute of Pharmacy and Biochemistry, Dolni, Mecholupy 130, 102 37 Prague, Czech Republic

A new synthesis of tert-butyl [(4R,6R)-6-aminoethyl-2,2-dimethyl-1,3-dioxan-4-yl]acetate based on the Henry reaction of nitromethane and tert-butyl [(4R,6S)-6-formyl-2,2-dimethyl-1,3-dioxan-4-yl]acetate is described.

Abstract

Synth. Commun. 2003, 33, 2285

Novel one Pot Synthesis of 3-Acetyl-5-Hydroxy-2-Methylbenzofuran and 3-Acetyl-5-Hydroxy-2-Methylnaphthofuran and Synthesis of their Derivatives

Guru S. Gadaginamath,* Rajesh R. Kavali,^# and Shashikanth R. Pujar

Department of Chemistry, Karnatak University, Dharwad 580 003, India

3-Acetyl-5-hydroxy-2-methylbenzofuran 5 and 3-acetyl-5-hydroxy-2-methylnaphthofuran 7 were synthesized by one pot method.

Abstract

Synth. Commun. 2003, 33, 2293

Ultrasound-Assisted Nucleophilic Substitution Reaction of t-Alkyl Halides with Zinc and Titanium Thiocyanate

B. K. Bettadaiah, K. N. Gurudutt, and P. Srinivas*

Central Food Technological Research Institute, Mysore-570013, India

Ultrasound promotes nucleophilic substitution of t-alkyl halides with ambident thiocyanate nucleophile, in the form of its zinc or titanium thiocyanate, in dichloromethane under mild conditions to afford the corresponding thiocyanates selectively, in good to excellent yields.

Abstract

Synth. Commun. 2003, 33, 2301

Thermal Behaviors of Ionic Liquids Under Microwave Irradiation and their Application on Mirowave-Assisted Catalytic Beckmann Rearrangement of Ketoximes

Jae-Kyun Lee,¹ Dok-Chan Kim,² Choong Eui song,¹ and Sang-gi-Lee^1,*

¹Life Sciences Division, Korea Institute of Science and Technology, P.O. Box 131, Cheongryang, Seoul 130-650, Korea

²Department of Chemical Engineering, University of Seoul, Seoul 130-743, Korea

Abstract

Synth. Commun. 2003, 33, 2309

Microwave Assisted Knoevenagel Condensation Using Sodium Fluoride and Lithium Chloride as Catalysts Under Solvent-Free Conditions

K. Mogilaiah,* M. Prashanthi, G. Randheer Reddy, Ch. Srinivas Reddy, and N. Vasudeva Reddy

Department of Chemistry, Kakatiya University, Warangal-506 009, India

Knoevenagel condensation of aromatic aldehydes with active methylene compounds under microwave irradiation using NaF and LiCl as catalysts in the absence of solvent is reported.

Abstract

Synth. Commun. 2003, 33, 2313

A Facile Synthesis of 2-Aroylindoles by the Oxidation of 2-Arylmethylindoles using Sarett Reagent

Nagappan Arumugam¹ and Panayencheri C. Srinivasan^2,*

¹R & D Department, Amrutanjan Ltd., Chennai 600 004, India

²Department of Organic Chemistry, University of Madras, Guindy Campus, Chennai 600 025, India

A facile synthesis of 2-aroylindoles from 2-arylmethylindoles using sarett reagent has been reported. The phenylthio at 3-position remains unaffected.

Abstract

Synth. Commun. 2003, 33, 2321

Conversion of Thiiranes to β-Chlorothioacetates Catalyzed with CoCl ₂

N. Iranpoor,* H. Firouzabadi* and A. A. Jafari

Chemistry Department, College of Science, Shiraz University, Shiraz 71454, Iran

Anhydrous cobalt(II) chloride catalyzes the ring opening of thiiranes with acetyl chloride to produce vicinal chlorothioesters in good yields.

Thiirane or R = (a) Ph; (b) cyclohexane oxide; (c) CH₂=CHCH₂OCH₂; (d) n-C₄H₉; (e) (CH₃)₂CHOCH₂; (f) ClCH₂; (g) PhOCH₂; (h) CH₂=CH(CH₃)CO₂CH₂

Abstract

Synth. Commun. 2003, 33, 2329

Synthesis of Some New 4-Substituted N-Benzyl-Piperidines

Gábor Dörnyei,* Mária Incze, István Moldvai, and Csaba Szántay

Institute of Chemistry, Chemical Research Center, Hungarian Academy of Sciences, 1025 Budapest, Pusztaszeri, út 59-67, Hungary

Synthesis of N-benzyl-4-piperidnne (4) via Knoevenagel condensation of N-benzyl-4-piperidone with malonitrile has been elaborated. The process is simple, inexpensive, and capable for scale up. Some new 4-substituted-N-benzyl-piperidines have been prepared and characterized.

Abstract

Synth. Commun. 2003, 33, 2339

Microwave Assisted Pictet–Spengler and Bischler–Napieralski Reactions

Bikash Pal, Parasuraman Jaisankar, and Venkatachalam S. Giri*

Department of Medicinal Chemistry, Indian Institute of Chemical Biology, 4 Raja S. C. Mullick Road, Calcutta-700 032, West Bengal, India

Abstract

Synth. Commun. 2003, 33, 2349

Studies on the Regioselective Reductive Ringcleavage Reactions of 3,5-O-Arylidene-d-Xylofuranosides

Ching-Yun Hsu* and Chia-Chun Chen

Department of Chemical Engineering, Cheng Shiu Institute of Technology Kaohsiung, Taiwan 833, ROC

Reductive ring cleavage of 3,5-O-arylidene-d-xylofuranosides using LiA1H₄–A1C1₃ and NaBH₃CN–BF₃ proceeded regioselectively to provide secondary alcohol as the major product. The effect of the substitutents on the selectivity is examined.

α-monomer R′=H, R′′=OCH₃; βanomer R′=OCH₃, R′′H Ar= (a) phenyl, (b) 4-methoxy phenyl, (c) 2,4-dimethoxy phenyl, (d) 2,6-dicholoro phenyl, (e) 2,6-difluoro phenyl

Abstract

Synth. Commun. 2003, 33, 2365

Direct Transformation of Allylic and Benzylic Thiols, Thioethers, and Disulfides into Organolithium Compounds

Miguel Yus,* Pedro Martínez, and David Guijarro

Departmento de Química Orgánica, Facultad de Ciencias, Universidad de Alicante, Apdo. 99, E-03080 Alicante, Spain

The reaction of allylic and benzylic thiols 1, disulfides 3, and thioethers 4 and 5 with an excess of lithium and a catalytic amount of DTBB, (5 mol%) afforded the corresponding allylic and benzylic organolithium reagents, which gave the expected products 2 by reaction with several electrophiles.