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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 33, 2003 - Issue 7
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Abstracts

Graphical Abstracts

Pages ix-xvi | Published online: 21 Aug 2006
 

Abstract

Synth. Commun. 2003, 33, 1067

Zeolite-HY Catalyzed Synthesis of 1,8-Naphthyridinyl-3(2H)-Pyridazinones in Dry Media Under Microwave Irradiation

K. Mogilaiah* and N. Vasudeva Reddy

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

An efficient microwave assisted solvent free zeolite-HY mediated synthesis of 1,8-naphthyridinyl-3(2H)-pyridazinones is reported.

Abstract

Synth. Commun. 2003, 33, 1073

Synthesis of Guanidine Derivatives and Molecular Recognition

Yanxing Qi, Haixiang Gao, Min Yang, Chun-Gu Xia, and Jishuan Suo*

State Key Laboratory for Oxo Synthesis and Selective Oxidation, Lanzhou Institute of Chemical Physics, Chinese Academy of Sciences, Lanzhou 730000, China

Five Guanidine Derivatives bearing acyl group were synthesized by the reaction of acyl chloride with 1,1,3,3-tetramethylguanidine. One of them (4a) was characterized by X-ray.

Abstract

Synth. Commun. 2003, 33, 1081

Synthesis of Kojic Acid Derivatives Containing Phenolic Hydroxy Groups

J. Kadokawa,1,* T. Nishikura,1 R. Muraoka,1 H. Tagaya,1 and N. Fukuoka2

1Department of Chemistry and Chemical Engineering, Faculty of Engineering, Yamagata University, Yonezawa 992-8510, Japan

2Chemipro Kasei Kaisha Ltd., Chuo-ku, Kobe 650-0044, Japan

Abstract

Synth. Commun. 2003, 33, 1087

A New Entry for the Preparation of Substituted Aromatic Carbonyl Compounds Mediated by Samarium(II) Iodide

Hidemi Yoda,* Naoki Kohata, and Kunihiko Takabe

Department of Molecular Science, Faculty of Engineering, Shizuoka University, Johoku 3-5-1, Hamamatsu 432-8561, Japan

Abstract

Synth. Commun. 2003, 33, 1095

Synthesis of Functionalized 2,3-Dihydropyrroles Promoted by Samarium Diiodide

Xiaoliang Xu1 and Yongmin Zhang1,2,*

1Department of Chemistry, Zhejiang University (Campus Xixi), Hangzhou, 310028, P.R. China

2State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, Shanghai, 200032, P.R. China

The intermolecular reductive coupling of 1,1-diaryl-2,2-dicyanoethylenes or 1,1-diaryl-2-cyano-2-ethoxycarbonylethylenes with substituted benzalazines induced by samarium diiodide was studied. Functionalized 2,3-dihydropyrroles were prepared in good yields under neutral and mild conditions.

Abstract

Synth. Commun. 2003, 33, 1103

Efficient Synthesis of Tolunitriles by Selective Ammoxidation

Guangyong Xie, Qiong Zheng,* Chi Huang, and Yuanyin Chen

College of Chemistry and Molecular Sciences, Wuhan University, Wuhan 430072, P.R. China

A route to prepare tolunitriles effectively by selective ammoxidation of methylbenzyl chlorides is reported.

Abstract

Synth. Commun. 2003, 33, 1109

One-Pot Synthesis of dl-2-Amino-2-thiazoline-4-carboxylic Acid

Richeng Xuan,* Weixiao Hu, and Zhongyu Yang

Institute of Pharmaceutical Engineering, Zhejiang University of Technology, Hangzhou-310014, P.R. China

dl-2-Amino-2-thiazoline-4-carboxylic acid was prepared in one-pot reaction from 2,3-dichloropropionic acid. Not only the procedure was simplified, but also the yield overall was increased from less than 63% recorded to 93%.

Abstract

Synth. Commun. 2003, 33, 1113

Synthesis of Novel Multifunctional Pyridine-2,6-Dicarboxylic Acid Derivatives

Xian-Hong Yin1,2,* and Min-Yu Tan2

1Department of Chemistry, Guangxi University for Nationalities, Nanning-530006, P.R. China

2Department of Chemistry, LanZhou University, LanZhou-730000, P.R. China

Eleven novel multifunctional compounds with pyridine-2,6-dicarboxylic acid were synthesized by hydrolyzing of ester prepared by coupling of diethyl 4-hydroxypyridine-2,6-dicarboxylate to bis-halohydrocarbon or bis-halide.

Abstract

Synth. Commun. 2003, 33, 1121

An Efficient Method for the Synthesis of (+)-Cyclozonarone, Isozonarol Δ,8,9 and Isozonarone Δ8,9

José Villamizar,* Juan Fuentes, Eleonora Tropper, Angel L. Orcajo, and Randolph Alonso

Centro de Química, Instituto Venezolano de Investigaciones Científicas (I.V.I.C.), Apartado 21827, Caracas, 1020-A, Venezuela

An efficient method for the synthesis of (+)-cyclozonarone 5, isozonarol Δ8,9 6 and isozonarone Δ8,9 7 via the diene 4, obtained in two steps from manool 3, is described.

Abstract

Synth. Commun. 2003, 33, 1131

A Novel Entry into a New Class of Spiro Heterocyclic Framework: A Facile Synthesis of Dispiro[Oxindole-1,2,3,4-Tetrahydro-naphthalen-1-one]pyrrolidines and Spiro[1,2,3,4-tetrahydro-naphthalen-1-one]pyrrolidines

A. Amal Raj and R. Raghunathan*

Department of Organic Chemistry, University of Madras, Guindy Campus, Chennai-25, India

Abstract

Synth. Commun. 2003, 33, 1141

A Synthesis of Captopril Through a Baylis–Hillman Reaction

Melissa P. Feltrin and Wanda P. Almeida*

Instituto de Ciências da Saúde, Universidade Paulista, Av. Comendador Enzo Ferrari, 280, Swift, Campinas, SP, CEP 13043-055, Brazil

In this work we descrbe an alternative route to the antihipertensive drug 1 (Captopril). The strategy is based on a Baylis–Hillman reaction between N-acryloylproline and 3 formaldehyde. A diastereoselective hydrogenation followed by functional group interconversion gave captopril.

Abstract

Synth. Commun. 2003, 33, 1147

A Short and Efficient Synthesis of Mono-Substituted 1,4,7-Triazacyclononanes

Hyun-soon Chong and Martin W. Brechbiel*

Chemistry Section, Radiation Oncology Branch, National Cancer Institute, Building 10, Rm B3B69, NIH, Bethesda, MD 20892

A convenient synthesis of 1,4,7-Triazacyclononane (tacn) derivatives substituted with a single pendant donor group is described.

Abstract

Synth. Commun. 2003, 33, 1155

Synthesis of Some Pyridazine Glycosides

Jun-Qian Feng,1 Chang-Jun Sun,2,* and Li-Qiang Qu2

1Scientific Research Institution of Jinan Refinery, Jinan, 250101, P.R. China

2School of Chemistry and Chemical Engineering, Shandong University, Jinan, 250100, P.R. China

Two N-glycosides 3(A, C) of 6-(4-methoxyphenyl)-3(2H)-pyridazinone 2 and two O-glycosides 6(A, B) of 6-(4-hydroxyphenyl)-4,5-dihydro-3(2H)-pyridazinone 5 were synthesized under phase transfer catalysis. Three O-glycosides 8(A–C) of 2 were prepared by the Koenigs-Knoor reaction of 1(A–C) with the silver salt 7 of 2. The compounds 3A, 8(A–C) were treated by ammonia to obtain four new compounds 4A′, 9(A′–C′).

Abstract

Synth. Commun. 2003, 33, 1163

Condensation of 2-Cyanomethylbenzoic Acid with Secondary Amines as a Method of Synthesis of 3-Amino-1,2-dihydro-1-isoquinolinone Derivatives

Tatyana Kucherenko, Volodimir Kysil, and Volodimir Kovtunenko*

Department of Chemistry, Kiyv Taras Shevchenko University, Kiyv, Vladimirskaya Street, 64, 01033, Ukraine

A simple one-stage method of preparation of 1,2-dihydro-1-isoquinolinone derivatives was proposed by condensation of 2-cyanomethylbenzoic acid with secondary amines.

Abstract

Synth. Commun. 2003, 33, 1167

An Efficient Strategy for the Synthesis of Chiral Liquid Crystals Using Evans' Methodology

Aloir A. Merlo* and Mirele S. Fernandes

Chemistry Institute, Federal University of Rio Grande do Sul, Campus do Vale, 91501 970-Porto Alegre, RS, Brazil

The synthesis of liquid crystal compound 2 was achieved using Evans' methodology.

Abstract

Synth. Commun. 2003, 33, 1179

Microwave-Assisted Synthesis of 10-Substituted Isoalloxazines in the Presence of Solid Acids

S. M. S. Chauhan,* Ram Singh, and Geetanjali

Department of Chemistry, University of Delhi, Delhi-110007, India

The microwave-enhanced synthesis of 10-substituted isoalloxazines is achieved rapidly and in good yield (>80–95%).

Abstract

Synth. Commun. 2003, 33, 1185

Introduction of a Carbohydrate Moiety into the Structure of Thiourea Compounds Targeting HIV-1 Reverse Transcriptase

P. Mallikarjun Goud, T. K. Venkatachalam, and F. M. Uckun*

Department of Chemistry, Parker Hughes Institute, Roseville, MN, 55113, USA

A novel approach for introduction of a carbohydrate moiety into the structure of non-nucleoside inhibitors (NNI) of HIV-1 reverse transcriptase.

Abstract

Synth. Commun. 2003, 33, 1195

Two-Carbons Homologation of Methyl Ketones Examplified for the Synthesis of Citral from 6-Methyl-5-hepten-2-one

Alain Valla,1,* Dominique Cartier,1Alain Laurent,1Benoist Valla,1Roger Labia,1and Pierre Potier2

1Chimie et Biologie des Substances Naturelles, FRE 2125 CNRS 6, Quimper, France

2Institut de Chimie des Substances Naturelles, UPR 2301 CNRS, Gif-sur-Yvette Cedex, France

New facile syntheses of 3,7-dimethyl-octadien-2,6-al (citral) from homologation of 6-methyl-5-hepten-2-one are reported.

Abstract

Synth. Commun. 2003, 33, 1203

Synthesis of a New Bisnorcholanic Lactone

José L. Mola Garate, Leticia Suárez García, Carlos S. Pérez Martinez, Martín A. Iglesias-Arteaga,* Deysma Coll Herrera, and Francisco Coll Manchado

Laboratorio de Productos Naturales, Facultad de Química, Universidad de la Habana, Zapata y G, C. Habana 10400, La Habana, Cuba

The synthesis and spectroscopic characterization of a new bioactive steroid with bisnorcholanic 22→16 lactone moiety are described.

Abstract

Synth. Commun. 2003, 33, 1211

Syntheses of 4-(3,5-Bisphenylmethylene-4-oxo-piperidin-1-yl)-4-oxo-but-2z-enoic Acid Arylamides as Candidate Cytotoxic Agents

Amitabh Jha*a# and Jonathan R. Dimmock*

College of Pharmacy and Nutrition, University of Saskatchewan, Saskatoon, SK S7N 5C9 Canada

The title compounds (A) were designed and synthesized as candidate cytotoxic agents. They were synthesized by reacting 3,5-bisphenylmethylene-4-oxo-piperidine (B) with the appropriate 3-arylcarbamoyl-acrylic acids (C). These reactions follow an unusual mechanism and deviate from the previously reported reactions on similar substrates.

Abstract

Synth. Commun. 2003, 33, 1225

An Improved Synthesis of Canthin-6-one

Kevin M. Czerwinski, Craig A. Zificsak, John Stevens, Melissa Oberbeck, Christopher Randlett, Melissa King, and Steve Mennen

Department of Chemistry, University of Wisconsin-Stevens Point, Stevens Point, WI 54481 USA

An improved route has been devised which provides canthin-6-one in the highest yield from tryptamine to date. Tryptamine is converted to Nb-benzyltryptamine via reaction with benzoylchloride and reduction using LAH. Pictet-Spengler condensation with 2-ketoglutaric acid, removal of the protecting group by CTH, and aromatization with MnO2 affords canthin-6-one in 48% overall yield.

Abstract

Synth. Commun. 2003, 33, 1233

An Improved Transient Method for the Synthesis of N-Benzoylated Nucleosides

Xue-Feng Zhu, Howard J. Williams Jr., and A. Ian Scott*

Center for Biological NMR, Department of Chemistry, Texas A & M University, P.O. Box 30012, College Station, TX-77842-3012, USA

The Jones' transient method for the synthesis of N-benzoylated nucleosides is improved by reducing the amounts of reagents and further simplified by omitting the addition of ammonium hydroxide.

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