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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 35, 2005 - Issue 13
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Abstracts

Graphical Abstracts

Pages i-vi | Published online: 15 Aug 2006
 

Abstract

Synth. Commun. 2005, 35, 1735

First Total Synthesis of Desmosdumotin C

Kyoko Nakagawa‐Goto,1 Jiu‐Hong Wu,2 and Kuo‐Hsiung Lee1

1Natural Products Laboratory, School of Pharmacy, University of North Carolina, Chapel Hill, North Carolina 27599‐7360, USA

2Department of Pharmacy, 306 Hospital, Beijing 100101, China

Desmosdumotin C (1), a novel compound isolated from the roots of Desmos dumosus, was synthesized from 2,4,6‐trihydroxyacetophenone (2), confirming the assigned structure of the natural product.

Abstract

Synth. Commun. 2005, 35, 1741

Organic Reactions in Ionic Liquids: Ionic Liquid‐Accelerated One‐Pot Synthesis of 2‐Arylimidazo[1,2‐a]Pyrimidine

Yuan‐Yuan Xie

College of Pharmaceutical Sciences, Zhejiang University of Technology, Hangzhou, China

The room‐temperature ionic liquid n‐butylpyridinium tetrafluoroborate (BPyBF4) is used as a recyclable alternative to classical molecular solvents in the one‐pot synthesis of 2‐arylimidazo[1,2‐a]pyrimidines by reaction with ketones, [hydroxy(tosyloxy)iodo]benzene, and 2‐aminopyrimidine. Significant rate enhancements and improved yields have been observed.

Abstract

Synth. Commun. 2005, 35, 1747

Synthesis of Novel Spiroheterocyclic Framework via the Regioselective 1,3‐Dipolar Cycloaddition Reaction of Azomethine Ylides

Xiao‐Fen Hu and Ya‐Qing Feng

Department of Fine Chemicals, School of Chemical Engineering, Tianjin University, Tianjin, China

A new series of dispiro pyrrolidines 4 have been synthesized by the regioselective cycloaddition of azomethine ylides with compounds 1 in good yield.

Abstract

Synth. Commun. 2005, 35, 1753

Synthesis of Thiazolo[2,3‐c]‐s‐Triazoles Using Poly[(4‐Diacetoxyiodo)Styrene]

Shi‐juan Liu,1 Ji‐zhen Zhang,2 Guan‐rong Tian,3 and Ping Liu3

1College of Chemistry, Jilin Normal University, Siping, China

2Provincial Key Constructive Laboratory of Precious Metals Processing Technology and Application, Jiangsu Teachers University of Technology, Changzhou, China

3Department of Chemistry, Yanbian University, Yanji, Ji Lin, China

Abstract

Synth. Commun. 2005, 35, 1759

Rapid and High‐Yield Synthesis of Aryloxyacetates under Microwave Irradiation and Phase‐Transfer Catalysis Conditions

Tai‐Bao Wei, Hong Liu, Man‐Lin Li, and You‐Ming Zhang

Department of Chemistry, Gansu Key Laboratory of Polymer Materials, Northwest Normal University, Lanzhou, Gansu 730070, China

A series of methyl aryloxyacetates (3a3f) have been synthesized by the reaction of substituted phenol with methyl chloroacetate under the conditions of microwave irradiation and phase‐transfer catalysis. By the optimization of the reaction conditions, we developed a good method for the preparation of methyl aryloxyacetates, which have the advantages of high yields, short reaction times, ease of workup, and simple operation.

Abstract

Synth. Commun. 2005, 35, 1765

Unusual p‐Toluene Sulfonic Acid–Catalyzed Carbon–Carbon Bond Formation

Shanmugam Govindan,1 Madhavi Maddipatla,1 Anil Kumar Podichetty,1 Prabhakahr Macharla,1 Venu Nalivela,1 Venkataraman Sundaram,1 Vijayavitthal T Mathad,1 Mahesh Reddy Ghanta,1 and Ravindra Kumar Yalavarti2

1Department of Research and Development, Dr. Reddy's Laboratories Ltd., S. V. Co‐Op. Ind. Estate, Bollaram, Jinnaram, Medak Dist., A.P., India

2Department of Analytical Research, Dr. Reddy's Laboratories Ltd., S. V. Co‐Op. Ind. Estate, Bollaram, Jinnaram, Medak Dist., A.P., India

Abstract

Synth. Commun. 2005, 35, 1769

Synthesis of Sporochnol A, a Marine Fish Deterrent

Bidyut Biswas and Ramanathapuram V. Venkateswaran

Department of Organic Chemistry, Indian Association for the Cultivation of Science, Jadavpur, Kolkatta 700 032, India

A synthesis of the methyl ether of the fish‐deterrent sporochnol A is described. The route involves the application of Claisen ortho‐ester rearrangement to generate the key quaternary carbon.

Abstract

Synth. Commun. 2005, 35, 1781

Facile and Simple Route to the Synthesis of Condensed Acridine Systems

Periyasamy Murugan,1 Kuo Chu Hwang,1 Dhakshanamurthy Thirumalai,2 and Vayalakavoor T. Ramakrishnan2

1Department of Chemistry, National Tsing Hua University, Hsinchu, Taiwan, China

2Department of Organic Chemistry, University of Madras, Chennai, India

Condensation of cyclohexane‐1,3‐dione or dimedone with o‐nitrobenzaldehyde and ammonium acetate/acetic anhydride furnished the corresponding acridinedione/xanthene derivatives. The middle ring aromatization followed by reductive cyclization afforded the respective condensed acridine systems.

Abstract

Synth. Commun. 2005, 35, 1789

Tetrahydropyranylation and Depyranylation of Alcohols Catalyzed by Aqueous Zinc Tetrafluoroborate

Samimul Islam,1 Adinath Majee,1 and A. T. Khan2

1Department of Chemistry, Visva‐Bharati, Santiniketan, West Bengal, India

2Department of Chemistry, Indian Institute of Technology, North Guwahati, Guwahati, India

Abstract

Synth. Commun. 2005, 35, 1795

MW‐Enhanced High‐Speed Deprotection of Boc Group using p‐TsOH and Concommitant Formation of N‐Me‐Amino Acid Benzyl Ester p‐TsOH Salts

Vommina V. Suresh Babu, Basanagoud S. Patil and Ganga‐Ramu Vasanthakumar

Department of Studies in Chemistry, Bangalore University, Bangalore, India

A high‐speed, complete deprotection of Boc group grom Boc‐amino acids and protected peptide esters employing p‐TsOH in toluene under microwave irradiation and synthesis of N‐Me amino acid benzyl esters starting from Boc‐N‐Me amino acids in a single step is carried out.

Abstract

Synth. Commun. 2005, 35, 1803

Novel and Efficient Synthesis of Water‐Soluble [60]Fullerenol by Solvent‐Free Reaction

Sheng Wang,1 Ping He,2 Jian‐Min Zhang,1 Hu Jiang,1 and Shi‐Zheng Zhu2

1Department of Chemistry, School of Science, Shanghai University, Shanghai, China

2Key Laboratory of Organofluorine Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Science, Shanghai, China

Water‐soluble fullerenol was conveniently synthesized via the direct solvent‐free reaction of fullerene with a mixture of H2O2 and NaOH under grinding conditions in air at room temperature. This practical method provides a novel convenient and efficient access to water‐soluble fullerenol in excellent yield.

Abstract

Synth. Commun. 2005, 35, 1809

Epoxidation of Protected (1,4,5)‐Cyclohex‐2‐ene‐triols and Their Acid Hydrolysis to Synthesize Quercitols from D‐( − )‐Quinic Acid

Tzenge‐Lien Shih and Ya‐Ling Lin

Department of Chemistry, Tamkang University, Tamsui, 25137 Taipei County, Taiwan, Republic of China

Abstract

Synth. Commun. 2005, 35, 1819

Enantioselective Addition of Diethylzinc to Aromatic Aldehydes Catalyzed by New Chiral Oxazolidine Ligand

Yong‐feng Kang,1 Lei Liu,1 Rui Wang,1,2 Ming Ni,1 and Zhi‐jian Han1

1Department of Biochemistry and Molecular Biology, School of Life Sciences, Lanzhou University, Lanzhou, Gansu, China

2State Key Laboratory for Oxo Synthesis and Selective Oxidation, Lanzhou Institute of Chemical Physics, Chinese Academy of Sciences, Lanzhou, Gansu, China

Abstract

Synth. Commun. 2005, 35, 1825

Preparation of 4‐Arylcyclopentenes by Sequential Diallylation of Arylaldehydes and Ring‐Closing Metathesis

Anne‐Catherine Durand,1 Lamia Brahmi,2 Mokhtar Lahrech,2 Salih Hacini,2 and Maurice Santelli1

1Laboratoire de Synthèse Organique, UMR 6180 CNRS and Université Paul Cézanne (Aix‐Marseille III): Chirotechnologies: Catalyse et biocatalyse, Faculté de St‐Jérôme, Marseille, France

2Laboratoire de Synthèse Organique, Université d'Oran Es Sénia, Oran, Algérie

Abstract

Synth. Commun. 2005, 35, 1835

Efficient Hexamethylenetetramine‐Bromine (HMTAB)‐Catalyzed Synthesis of Bis(indolyl)Methanes in Water

Mohammad Bagher Teimouri and Houri Mivehchi

Iran Polymer and Petrochemical Institute, Tehran, Iran

Abstract

Synth. Commun. 2005, 35, 1845

Facile and Inexpensive Entry to Indeno[2,1‐b]indol‐6‐one Nucleus

Giorgio Abbiati, Valentina Canevari, Elisabetta Rossi and Alberto Ruggeri

Istituto di Chimica Organica “Alessandro Marchesini,” Facoltà di Farmacia, Università degli Studi di Milano, Milan, Italy

Abstract

Synth. Commun. 2005, 35, 1851

Homocoupling of Aryl Iodides and Bromides Using a Palladium/Indium Bimetallic System

Yu Mi Chang,1 Seung Hwan Lee,1 Min Young Cho,2 Byung Woo Yoo,2 Hak June Rhee,3 Sang Ho Lee,1 and Cheol Min Yoon2

1Graduate School of Biotechnology, Korea University, South Korea

2Department of New Material Chemistry, Korea University, South Korea

3College of Science and Technology, Hanyang University, South Korea

Homocoupling of aryl iodides and bromides using catalytic amounts of palladium and stoichiometric amounts of indium proceeded smoothly to afford the corresponding biaryls in good to high yields.

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