Graphical Abstracts

Abstract

Synth. Commun. 2003, 33, 1969

An Efficient One-Pot Synthesis of 2-Hydroxyalkyl Dithiocarbamates

Jia-ling Cui, Ze-mei Ge, Tie-ming Cheng, and Runtao Li*

School of Pharmaceutical Sciences, Peking University, Xueyuan Road 38, Haidian District, Beijing, 100083, P.R. China

In the presence of anhydrous potassium phosphate, epoxides reacted with carbon disulfide and primary or secondary amines in acetone to give the corresponding 2-hydroxyalkyl dithiocarbamates regioselectively in moderate to good yield.

Abstract

Synth. Commun. 2003, 33, 1977

Design and Synthesis of Heterocyclic Hydroxamic Acid Derivatives as Inhibitors of Helicobacter pylori Urease

Estela Maris F. Muri, Hetal Mishra, Mitchell A. Avery, and John S. Williamson*

Faser Hall, School of Pharmacy, Department of Medicinal Chemistry, University of Mississippi, University, MS 38677, USA

Various heterocyclic hydroxamic acid derivatives were designed and synthesized as H. pylori inhibitors.

Abstract

Synth. Commun. 2003, 33, 1997

Conversion of Alkynes into α,α-Dichloro Ketones and α,α-Dichlorodimethyl Ketals Using Trichloroisocyanuric Acid

Gene A. Hiegel,* Christopher D. Bayne, and Brendt Ridley

Department of Chemistry and Biochemistry, California State University, 800 N. State College Blvd., Fullerton, California 92834, USA

Trichloroisocyanuric acid (TICCA) reacts with alkynes in the presence of water in acetone or acetonitrile to form α,α-dichloro ketones and in methanol to form α,α-dichlorodimethyl ketals.

Abstract

Synth. Commun. 2003, 33, 2003

The Oxidation of Primary Alcohols to Methyl Esters and Diols to Lactones Using Trichloroisocyanuric Acid

Gene A. Hiegel* and Cynthia B. Gilley

Department of Chemistry and Biochemistry, California State University, 800 N. State College Blvd., Fullerton, California 92834, USA

Primary alcohols and diols are easily oxidized to methyl esters by a solution of trichloroisocyanuric acid with methyl alcohol in dichloromethane. In addition, α,ω-diols are also readily oxidized into lactones by refluxing with trichloroisocyanuric acid and pyridine in dichloromethane.

Abstract

Synth. Commun. 2003, 33, 2011

Aqueous Trichloroacetic Acid: Another Useful Reagent for Highly Selective 5′-Desilylation of Multisilylated Nucleosides

Xue-Feng Zhu, Howard J. Williams, 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

Highly selective 5′-desilylation of multisilylated nucleosides can be achieved in excellent yield by treatment with 4.2 M aqueous trichloroacetic acid:THF (1:4).

Abstract

Synth. Commun. 2003, 33, 2017

Ultrasound-Assisted Epoxidation of Olefins and α,β-Unsaturated Ketones over Hydrotalcites Using Hydrogen Peroxide

Unnikrishnan R. Pillai, Endalkachew Sahle-Demessie,* and Rajender S. Varma

National Risk Management Research Laboratory, Sustainable Technology Division, MS 443, United States Environmental Protection Agency, 26 W. Martin Luther King Drive, Cincinnati, OH 45268, USA

Abstract

Synth. Commun. 2003, 33, 2029

Novel Synthesis of 1-(1,2,3,5,6,7-Hexahydro- s -Indacen-4-Yl)-3-[4-(1-Hydroxy-1-Methyl-Ethyl)-furan-2-sulfonyl] urea, an Anti-Inflammatory Agent

Frank J. Urban,* V. John Jasys, Jeffrey W. Raggon, Richard A. Buzon, Paul D. Hill, James F. Eggler, and John D. Weaver

Pfizer Global Research and Development, Chemical Research and Development, Eastern Point Road, Groton, CT 06340, USA

Abstract

Synth. Commun. 2003, 33, 2045

Improved Synthesis of Dialkylaminopyrrolines

David A. Flosser and Roy A. Olofson*

The Pennsylvania State University, Department of Chemistry, University Park, PA 16802, USA

The literature synthesis of 5-dialkylamino-3,4-dihydro-2H-pyrroles has been substantially improved. Alkylation of these amidines affords pyrrolinium halides which in initial assays show promise as “naked halide” catalysts.

Abstract

Synth. Commun. 2003, 33, 2053

The Synthesis of Aminobenzothiazoles from 2,3-Biaryl-5-anilino-Δ³-1,2,4-thiadiazolines

Kevin Pan* and Allen B. Reitz

Drug Discovery Division, The R.W. Johnson Pharmaceutical Research Institute, Welsh and McKean Roads, P.O. Box 776, Spring House, PA 19477-0776, USA

2-Amidinobenzothiazoles 4 can be prepared in high yields by a thermally-promoted rearrangement of thiadiazolium salts 1 or thiadiazolines 2. Addition of base to the rearrangement of the thiadiazolium salts can improve the yields by the prior conversion of the thiadiazolium salts to the corresponding thiadiazoline free bases. The rearrangement of the thiadiazolines may go through an electrophilic aromatic substitution or free radical pathway.

Abstract

Synth. Commun. 2003, 33, 2061

ortho-(Substituted Silyl)phenylsydnones via a Novel Sydnone to Phenyl Ring, Lithiation-Induced Silicon Migration

Kenneth Turnbull* and Douglas M. Krein

Chemistry Department, Wright State University, 3640 Colonel Glenn Highway, Dayton, Ohio 45435, USA

3-(2-Bromophenyl)sydnone (5) reacts with LDA then substituted chlorosilanes to form the corresponding 4-silylsydnones 6, which rearrange to the novel ortho-silylphenylsydnones 8 on treatment with n-butyllithium.

Abstract

Synth. Commun. 2003, 33, 2069

An Efficient Separation Method for Enol Phosphate and Corresponding β-Ketophosphonate from Their Mixtures Under Aqueous Conditions

Cornelis M. Moorhoff*

Department of Chemistry, The University of Tasmania, GPO Box 252-75, Hobart, Tasmania, 7001, Australia

Separation of mixtures β-ketophosphonate 3 and their corresponding enol phosphate 4 is efficiently carried out in aqueous alkaline solutions.

Abstract

Synth. Commun. 2003, 33, 2087

Reaction of Oxime derivatives of β-diketones and β-keto-esters with substituted hydrazides: novel synthesis of nitroso-N-sulfonyl- and nitroso-N-substituted amino pyridones

Galal H. Elgemeie^1,* and Ali M. Elzanate²

¹Chemistry Department, Faculty of Science, Helwan University, Ain-Helwan, Helwan, Cairo, Egypt

²Chemistry Department, Faculty of Science, Cairo University (Beni-Suef Branch), Beni-Suef, Egypt

Abstract

Synth. Commun. 2003, 33, 2095

A Novel Synthesis of N-Aryl-6-Methylsulfanyl-4-Pyrimidinones and Purine Analogues: The Reaction of Dimethyl N-Cyanodithioiminocarbonate with Cyanoacetanilides

Galal H. Elgemeie,* Samia R. El-Ezbawy, and Soha A. Sood

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

Abstract

Synth. Commun. 2003, 33, 2103

A Highly Efficient and Chemoselective Method for Acetalization of Carbonyl Compounds Catalyzed by Solid Superacid

Yan-Ran Ma, Tong-Shou Jin,* Sheng-Xun Shi, and Tong-Shuang Li

Department of Chemistry, College of Chemistry and Environmental Science, Hebei University, No. 1 Hezuo Road, Baoding 071002, P.R. China

Various types of aldehydes and ketones could be converted to their corresponding diethyl acetals with triethylorthoformate in the presence of solid superacid in good to excellent yields under mild reaction conditions.

Abstract

Synth. Commun. 2003, 33, 2109

Synthesis of 5-Carbonyl-1,3-dihydro-1,3-dioxo-2H-isoindole-2-Propanoic Acid Integrin Antagonists

Yong Deng,^1,* Yi Shen,² and Yu-Guo Zhong²

¹Department of Pharmaceutical Engineering, College of Chemical Engineering, Sichuan University, Chengdu, Sichuan, 610065, P.R. China

²Department of Medicinal Chemistry, West China School of Pharmacy, Sichuan University, Chengdu, Sichuan, 610041, P.R. China

5-Carbonyl-1,3-dihydro-1,3-dioxo-2H-isoindole-2-propanoic acid derivatives (IV), have been synthesized and the structure of these compounds were established by elemental analysis, IR, MS, and ¹HNMR spectral data.

Abstract

Synth. Commun. 2003, 33, 2119

Synthesis of 2-Bromo-2′-Phenyl-5,5′-Thiophene: Suzuki Reaction Versus Negishi Reaction

Nai-Xing Wang*

Institute of Photographic Chemistry, Chinese Academy of Sciences, Beijing 100101, P.R. China

2-Bromo-2′-phenyl-5,5′-bithiophene was synthesized by cross-coupling reaction of phenylboric acid and 2,2′-dibromo-5,5′-bithiophene.

Abstract

Synth. Commun. 2003, 33, 2125

A Convenient, Large Scale Synthesis of trans-(bplus;)-Sobrerol

Qiuan Wang,¹ Yanlin Li, ¹ and Qingqi Chen^2,*

¹College of Chemistry and Chemical Engineering, Hunan University, Changsha 410082, P.R. China

²Biomarin Pharmaceutical Inc., 2386 East Mall, Vancouver, BC, V6T 1Z3, Canada

The synthesis of optically pure trans-(+)-sobrerol (1), starting from methyl 3,5-dihydroxy-4-methyl benzoate 2 in 8 steps with overall yield 26%, is described.

Abstract

Synth. Commun. 2003, 33, 2135

“Instant Methylide” Modification of the Corey–Chaykovsky Epoxide Synthesis

James A. Ciaccio,* Antoinette L. Drahus,^# Regina M. Meis, Carice T. Tingle, Michael Smrtka, and Richard Geneste

Department of Chemistry, Fordham University, Bronx, New York 10458, USA

Abstract

Synth. Commun. 2003, 33, 2145

Preparation of a Series of Aryl Isonipecotic Acids Using Microwave Irradiation

Schuyler Antane*

Chemical Sciences, Wyeth Research, CN 8000, Princeton, New Jersey 08543-8000, USA

Ethyl isonipecotate (1) was coupled with substituted aryl bromides (2) under microwave conditions, then hydrolyzed to prepare a series of aryl isonipecotic acids (3).

Abstract

Synth. Commun. 2003, 33, 2151

Cannabinoid CB1 Receptor Chemical Affinity Probes: Methods Suitable for Preparation of Isopropyl [11,12-³H]Dodecylfluoro-phosphonate and [11,12-³H]Dodecanesulfonyl Fluoride

Yoffi Segall,^# Gary B. Quistad, and John E. Casida*

Environmental Chemistry and Toxicology Laboratory, Department of Environmental Science, Policy, and Management, 114 Wellman Hall, University of California, Berkeley, CA 94720-3112, USA

A suitable procedure is described for one-step radiolabeling of dodec-11-ene derivatives to make high-potency chemical affinity radioprobes for mouse brain cannabinoid CB1 receptor and fatty acid amide hydrolase.

Abstract

Synth. Commun. 2003, 33, 2161

Study Toward the Synthesis of Selenofurans via Seleno-Claisen Rearrangement of Allyl Arylselenides

Hélio A. Stefani,^1,* Nicola Petragnani,² Maria F. C. Ascenso,¹and Gilson Zeni³

¹Faculdade de Ciências Farmacêuticas, Departamento de Farmácia, Av. Prof. Lineu Prestes, 580-Bloco 13 Sup. 05508, and ²Instituto de Química, Universidade de São Paulo, São Paulo, SP—Brazil

³Departamento de Química, Universidade Federal de Santa Maria, Santa Maria, RS—Brazil

Abstract

Synth. Commun. 2003, 33, 2167

The Formation of 7-Oxabicyclo[4.2.0]octanes and 6-Oxabicyclo[3.2.1]octanes via Cationic Iodocyclization

Christopher J. Nichols*

Department of Chemistry, California State University, Chico, 400 W. 1st St., Chico, CA, USA 95929-0210

Several 2-cyclohexenemethanol derivatives were subjected to cationic iodocyclization. Two product types were formed: the fused 7-oxabicyclo[4.2.0]octane, and the bridged 6-oxabicyclo[3.2.1]octane. The degree of substitution in the alkenol determined the ratio of the products, with aromatic substituents leading to the formation of the fused system as the major product.