Graphical Abstracts
2003; Taylor & Francis; Volume: 33; Issue: 13 Linguagem: Inglês
10.1081/scc-120021494
ISSN1532-2432
Tópico(s)Asymmetric Synthesis and Catalysis
ResumoAbstract Synth. Commun. 2003, 33, 2181 Surface-Mediated Hydrohalogenation of Isoprene: A Facile Preparation of Prenyl Halides Marcio C. S. de Mattos1,* 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. 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. Synth. Commun. 2003, 33, 2197 Highly Diastereoselective Alkylation of the Dellaria Oxazinone Template with Bifunctional Electrophiles Gregory H. P. Roos1,* 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. 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. 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. 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. 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 Synth. Commun. 2003, 33, 2243 A New Class of Dihydropyridine Thioglycosides via Piperidinium Salts Adel M. Attia1 and Galal H. Elgemeie2,* 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. 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 Somfai1,* 1Organic Chemistry, Department of Chemistry, Royal Institute of Technology, S-100 44 Stockholm, Sweden 2Amersham Biosciences, S-751 84 Uppsala, Sweden 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 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 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. 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. 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. 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-Lee1,* 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 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. 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. Srinivasan2,* 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. 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 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. 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 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 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.
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