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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 35, 2005 - Issue 5
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Abstracts

Graphical Abstracts

Pages i-vi | Published online: 20 Aug 2006
 

Abstract

Synth. Commun. 2005, 35, 631

A Versatile One‐Pot Synthesis of Dialkyl Disulfides and Sulfides

David W. Emerson, Byron L. Bennett, and Spencer M. Steinberg

Department of Chemistry, University of Nevada, Las Vegas, Nevada, USA

1‐Bromo‐3‐fluoropropane reacted with thiourea to form an S‐alkyl‐thiuroium bromide. Addition of sodium hydroxide and hydrogen peroxide in situ yielded 3‐fluoro‐1‐propyl disulfide in 58% yield.

Abstract

Synth. Commun. 2005, 35, 639

Routes to Sydnone‐containing Oligomeric Areneynes

Andrew J. Weisner,1 Thomas M. Cooper,2 and Kenneth Turnbull1

1Chemistry Department, Wright State University, Dayton, Ohio, USA

2Materials and Manufacturing Directorate, Air Force Research Laboratory, Ohio, USA

Abstract

Synth. Commun. 2005, 35, 653

RuCl3 catalyzed one‐pot synthesis of α‐aminonitriles

Surya Kanta De

Department of Medicinal Chemistry and Molecular Pharmacology, School of Pharmacy, Purdue Cancer Center, Purdue University, West Lafayette, IN 47907, USA

Abstract

Synth. Commun. 2005, 35, 657

A Practical Synthesis of 3,3‐Difluorocyclobutane Carboxylic Acid

Dirk Elend, David Fengas, and M. Jonathan Fray

Discovery Chemistry Department, Pfizer Global Research and Development, Sandwich, Kent CT13 9NJ, UK

We report a straightforward, three step synthesis of 3,3‐difluorocyclobutane carboxylic acid.

Abstract

Synth. Commun. 2005, 35, 663

Modification of the Titanium(IV) Isopropoxide Reductive Amination Reaction: Application to Solid Phase Synthesis

John C. DiCesare, Celesta E. White, Wendy E. Rasmussen, Bryan M. White, Charles B. McComas, and Laura E. Craft

Department of Chemistry and Biochemistry, The University of Tulsa, Tulsa, OK 74104, USA

Secondary amines are synthesized by a modification of the titanium(IV) isopropoxide reductive amination reaction. The modified procedure has been utilized for both solution and solid phase synthesis with excellent purity and yields.

Abstract

Synth. Commun. 2005, 35, 669

Phase‐Transfer Catalyzed Pseudohalogenation of Phosphorochloridates

E. Shi and C. Pei

Beijing Institute of Pharmaceutical Chemistry, Beijing, P. R. China

Synthesis of phosphorazidates phosphorocyanidates, and phosphor(isothiocyanidate)s from pseudohalogenation of phosphorochloridates by sodium pseudohalides under two kinds of mild phase‐transfer catalyzed conditions is described.

Abstract

Synth. Commun. 2005, 35, 675

Microwave‐Assisted Facile Synthesis of Dispiro 4‐Imino‐1,3‐Dioxolanes

Mohammad Bagher Teimouri

Gas Conversion Department, Iran Polymer and Petrochemical Institute, Tehran, Iran

Abstract

Synth. Commun. 2005, 35, 683

Synthesis of New 9‐(N‐SUBSTITUTED)‐Acridinamines Bearing A Pendant Polymerizable Side Chain

Gabriel Roubaud, Sebastien Billeau, Robert Faure, Maxime Robin, and Jean‐Pierre Galy

UMR CNRS 6178 Symbio, Laboratoire de Valorisation de la Chimie Fine, Faculté des Sciences et Techniques de Saint Jérôme, Université Paul Cézanne, Av. Escadrille Normandie‐Niemen, 13397 Marseille Cedex 3, France

New 9‐(N‐substituted)‐acridinamines (7–11), have been synthesized from allyl 4‐(9‐chloro‐7‐methoxy‐2‐acridinyl)‐butanoate (6).

Abstract

Synth. Commun. 2005, 35, 693

An Easy Access to Variously Substituted Pyrroles Starting From Ketene Dithioacetals

Geoffroy L. Sommen,1 Alain Comel,2 and Gilbert Kirsch2

1Organisch‐Chemisches Institut der Universität Zürich, Zürich, Switzerland

2Laboratoire d'Ingénierie Moléculaire et Biochimie Pharmacologique, Faculté des Sciences, Université de Metz, Metz, France

Variously substituted pyrroles can easily be synthesized in two steps by reacting a primary or secondary amine and a ketene dithioacetal in a basic medium in moderate to good yield. Ketene dithioacetals are readily prepared from acetylaceton or malononitrile, carbon disulfide, and methyl iodide.

Abstract

Synth. Commun. 2005, 35, 701

Synthesis and Characterization of Thienorphine and its Glucuronide Conjugate

Chun‐He Liu, He Liu, Xiang‐Yu Han, Bo Wu, Bo‐Hua Zhong, and Ze‐Hui Gong

Beijing Institute of Pharmacology and Toxicology Academy, Beijing 100850, P. R. China

A potent mixed agonist and antagonist opiate receptor thienorphine and its glucuronide conjugate were synthesized. The structure of thienorphine was determined by X‐ray crystallography.

Abstract

Synth. Commun. 2005, 35, 711

Anodic Cyanation of (−)‐N‐Phenyl‐2‐Methylpiperidine: A Short Synthesis of (+)‐Solenopsin A and (+)‐Isosolenopsin A

Nicolas Girard,1 Jean‐Pierre Hurvois,1 Loic Toupet,2 and Claude Moinet1

1Laboratoire d'électrochimie, UMR 6509, Institut de Chimie, Université de Rennes I, Campus de Beaulieu, F‐35042 Rennes Cedex, France

2Groupe Matière Condensée et Matériaux, Université de Rennes I, Campus de Beaulieu, F‐35042 Rennes Cedex, France

Abstract

Synth. Commun. 2005, 35, 725

A Convenient Synthesis of 1‐Amino‐7‐(Piperidin‐4‐YL)Isoquinoline

Sergey Shkavrov, Sergey Popov, Dmitry Kravchenko, and Mikhail Krasavin

Chemical Diversity Research Institute, Khimki, Moscow Reg., 114401, Russia

An optimized synthesis of 2‐amino‐7‐(piperidin‐4‐yl)isoquinoline, starting from 4‐bromocinnamic acid, has been developed.

Abstract

Synth. Commun. 2005, 35, 731

Convenient Preparation of O‐Alkylhydroxamic Acids Using 2‐Acyl‐pyridazin‐3(2H)‐ones

Jeum‐Jong Kim,1 Young‐Dae Park,1 Ho‐Kyun Kim,1 Su‐Dong Cho,1 Ju‐Kyeong Kim,1 Sang‐Gyeong Lee,2 and Yong‐Jin Yoon1

1Department of Chemistry and Environmental Biotechnology National Core Research Center, Gyeongsang National University, Chinju, Korea

2Department of Chemistry and Research Institute of Life Science, Gyeongsang National University, Chinju, Korea

Abstract

Synth. Commun. 2005, 35, 739

Organic Reactions in Ionic Liquids: Ionic Liquids Ethylammonium Nitrate Promoted Knoevenagel Condensation of Aromatic Aldehydes with Active Methylene Compounds

Yi Hu,1,2 Jue Chen,1,2 Zhang‐Gao Le,1,2,3 and Qin‐Guo Zheng4

1Ningbo Institute of Technology, Zhejiang University, Ningbo, P. R. China

2Department of Chemistry, Zhejiang University (Xi Xi Campus), Hangzhou, P. R.China

3Department of Applied Chemistry, East China Institute of Technology, Fuzhou, P. R.China

4Pharmaceutical Science Research Institute, Aston University, Aston Triangle, Birmingham, UK

Abstract

Synth. Commun. 2005, 35, 745

Efficient Synthesis of γ‐Keto Esters from Enamines and EDA

Dan Huang,1,2 Ming Yan,1 Wei‐Jie Zhao,1 and Qi Shen1

1Department of Chemistry and Chemical Engineering, Suzhou University, Suzhou, Jiangsu, China

2Department of Chemistry, Nantong Teachers College, Nantong, Jiangsu, China

The reaction of enamines with ethyl diazoacetate (EDA) catalyzed by dirhodium and copper complexes provided γ‐keto esters in good yields.

Abstract

Synth. Commun. 2005, 35, 751

Asymmetric Cyanohydrin Synthesis Catalyzed by Mn(salen) Complex/Triphenylphosphine Oxide

Sung Soo Kim and Sang Hyuck Lee

Department of Chemistry and Center for Chemical Dynamics, Inha University, Incheon, South Korea

Various aldehydes have undergone asymmetrical trimethylsilylcyanation (TMSCN) with (CH3)3SiCN. The yield is over 90% in most cases and ee's range from 44% to 64% employing chiral Mn(salen) and triphenylphosphine oxide as the catalyst.

Abstract

Synth. Commun. 2005, 35, 761

Synthesis of Aromatic Thioamide from Nitrile without Handling of Gaseous Hydrogen Sulfide

Akira Manaka and Masakazu Sato

Medicinal Chemistry Laboratory, Medicinal Research Laboratories, Taisho Pharmaceutical Co. Ltd., 1‐403, Yoshino‐cho, Kita‐ku, Saitama, Japan

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