Graphical Abstracts

Abstract

Synth. Commun. 2004, 34, 1925

Facile Preparation of α‐Acyloxyacetaldehyde, a Versatile Intermediate in the Synthesis of Antiviral Nucleosides

Jinfa Du* and Kyoichi A. Watanabe

Pharmasset, Inc., Tucker, Georgia, USA

Abstract

Synth. Commun. 2004, 34, 1931

The Preparation of 2‐Arylmethylidene‐8‐Methyl‐8‐Azabicyclo[3.2.1]Octan‐3‐Ones

Guangrong Zheng, Linda P. Dwoskin, and Peter A. Crooks*

Department of Pharmaceutical Sciences, College of Pharmacy, University of Kentucky, Lexington, Kentucky, USA

An efficient and versatile two step synthesis of 2‐arylmethylidene‐8‐methyl‐8‐azabicyclo[3.2.1]octane‐3‐ones is described.

Abstract

Synth. Commun. 2004, 34, 1943

Diethylaluminum Chloride Mediated Vinylsilane Synthesis: Comparison of Different Solvent Systems

Man Lung Kwan,^1,* Merle A. Battiste,² Megan K. Macala,¹ Sylvia C. Aybar,³ Nicholas C. James, ¹ and Joseph J. Haoui¹

¹Department of Chemistry, John Carroll University, University Heights, Ohio, USA

²Department of Chemistry, University of Florida, Gainesville, Florida, USA

³Cuyahoga Community College, Highland Hills, Ohio, USA

Aromatic ketones were converted to one‐carbon elongated‐vinylsilanes in a convenient one‐pot operation via the Peterson protocol. Reactions were conducted in two different solvents for comparison: pentane and triethylamine. Results indicate that triethylamine appeared to be a more suitable solvent for such a transformation producing vinylsilanes with great chemo‐ and stereo‐selectivity than pentane.

Abstract

Synth. Commun. 2004, 34, 1951

Synthesis of Fused Tetrahydrofuran‐γ‐lactone Motifs via One‐Pot Ring Expansion of Cyclopropane Rings

Charles Kim, Thomas Brady, Sun Hee Kim, and Emmanuel A. Theodorakis*

Department of Chemistry, University of California San Diego, La Jolla, California, USA

The fused tetrahydropyran‐γ‐lactone structures, such as 8, were prepared in good yields by an acid‐induced ring expansion of the corresponding cyclopropyl precursors 6. Best yields were obtained using MeSO₃H in acetone.

Abstract

Synth. Commun. 2004, 34, 1967

Immediate and Efficient Oxidative Deprotection of Dithioacetals to Carbonyl Compounds by Zinc Dichromate Trihydrate (ZnCr₂O₇ · 3H₂O)

Habib Firouzabadi,* Nasser Iranpoor,* Hassan Hassani, and Sara Sobhani

Department of Chemistry, College of Sciences, Shiraz University, Shiraz, Iran

Zinc dichromate trihydrate (ZnCr₂O₇·3H₂O) is an efficient oxidizing agent for the immediate deprotection of 1,3‐dithianes, 1,3‐dithiolanes, and dibuthyl dithioacetals to their corresponding carbonyl compounds in non‐aqueuos and aprotic conditions at room temperature.

Abstract

Synth. Commun. 2004, 34, 1973

A Ring Expansion Strategy in Antiviral Synthesis: A Novel Approach to TAK‐779

Terrence L. Smalley Jr.*

GlaxoSmithKline, Inc., M&V CEDD Chemistry, Research Triangle Park, North Carolina, USA

A concise synthesis of a novel antiviral agent was completed with the key transformation being a ring expansion from a tetralone to a suberone.

Abstract

Synth. Commun. 2004, 34, 1981

A Convenient Preparation of Tetrahydrofuran‐based Diamines

Gaifa Lai*

Chemo Dynamics, Inc., Sayreville, New Jersey, USA

Abstract

Synth. Commun. 2004, 34, 1989

Efficient Sonochemical Synthesis of 3‐ and 4‐Electron Withdrawing Ring Substituted N‐Alkyl‐1,8‐naphthalimides from the Related Anhydrides

Eduardo R. Triboni,¹ Pedro Berci Filho^1,*, Roberto G. S. Berlinck¹, and Mario J. Politi²

¹Instituto de Química de São Carlos, Universidade de São Paulo, CP 780, São Carlos, SP, Brazil

²Instituto de Química, Universidade de São Paulo, São Paulo, SP Brazil

1,8‐N‐alkyl‐naphthalimides substituted with electron withdrawing groups were readily prepared in high yields using ultrasound in aqueous media.

Abstract

Synth. Commun. 2004, 34, 2001

Optimization of Allylic Oxidation of (1S,3R,8R)‐2,2‐dichloro‐3,7,7,10‐tetramethyltricyclo[6,4,0,0^1,3]dodec‐9‐ene

M. Dakir,^1,2 A. Auhmani,^1,* My. Y. Ait Itto,¹ N. Mazoir,¹ M. Akssira,² M. Pierrot,³ and A. Benharref¹

¹Laboratoire de Chimie des Substances Naturelles, Département de Chimie, Faculté des Sciences Semlalia, Marrakech, Morocco

²Laboratoire de Chimie Bio‐organique et Analytique, Faculté des Sciences et Techniques, Mohammedia, Morocco

³LBS‐UMR 6517, Centre Scientifique Saint‐Jérôme, Marseille, France

The allylic oxidation of (1S,3R,8R)‐2,2‐dichloro‐3,7,7,10‐tetramethyltricyclo[6,4,0,0^1,3]dodec‐9‐ene into the corresponding enone with N‐bromosuccinimide (NBS), CrO₃ and t‐BuOOH has been studied. A good yield and high selectivity were obtained in the presence of t‐BuOOH and a copper catalyst.

Abstract

Synth. Commun. 2004, 34, 2009

Synthesis of Hyperbranched Dendrimers with Hydrophobic Surface Group

Perumal Rajakumar* and Kilivelu Ganesan

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

Hyperbranched dendrimers were synthesized with m‐terphenyl end group.

Abstract

Synth. Commun. 2004, 34, 2019

A Simple Synthesis of Dibenzo[b,g][1,8]naphthyridines

N. Sampathkumar, N. Venkatesh Kumar and S. P. Rajendran*

Department of Chemistry, Bharathiar University, Coimbatore, Tamil Nadu, India

2‐Chloro‐3‐formyl quinoline and its derivatives on reaction with anilines in DMF afforded the dibenzo[b,g][1,8]naphthyridines.

Abstract

Synth. Commun. 2004, 34, 2025

One‐Pot Synthesis of Nitriles from Aldehydes and Hydroxylamine Hydrochloride Over Silica Gel, Montmorillonites K‐10, and KSF Catalysts in Dry Media Under Microwave Irradiation

Sharwan K, Dewan,* Ravinder Singh, and Anil Kumar

Department of Chemistry, M.D. University, Rohtak, Haryana, India

A rapid and facile one pot synthesis of nitriles has been carried out from the corresponding aldehydes and hydroxylamine hydrochloride in the presence of environmentally benign silica gel (84–95%), Mont K‐10 (85–96%) and Mont KSF clay (88–98%) catalysts in dry media under microwave irradiation.

Abstract

Synth. Commun. 2004, 34, 2031

An Advanced Intermediate for the Synthesis of (±)‐Pumiliotoxin C and its Analogues

Zhi‐Hui Shao,^1,2 Fang‐Zhi Peng,² Jing‐Bo Chen,² Chen‐Ying Wang,² Rong Huang,² Yong‐Qiang Tu,¹ Liang Li,² and Hong‐Bin Zhang²*

¹National Laboratory of Applied Organic Chemistry, Lanzhou University, Lanzhou, P.R. China

²School of Pharmacy, Yunnan University, Kunming, P.R. China

Abstract

Synth. Commun. 2004, 34, 2039

Organic Reactions in Ionic Liquids: an Efficient Method for Selective S‐Alkylation of 2‐Mercaptobenzothia(xa)zole with Alkyl Halides

Yi Hu,^1,2 Zhen‐Chu Chen,^1,2,* Zhang‐Gao Le,² and Qin‐Guo Zheng³

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

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

³Pharmaceutical Science Research Institute, Aston University, Birmingham, UK

Abstract

Synth. Commun. 2004, 34, 2047

Solvent‐Free Synthesis of Ethyl α‐Cyanocinnamate in the Presence of CaO

Yeying Lu,¹ Zhongjiao Ren,^1,* Weiguo Cao,^1,2 Weiqi Tong,¹ and Mengfei Gao¹

¹Department of Chemistry, Shanghai University, Shanghai, P.R. China

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

Ethyl α‐cyanocinnamate can be obtained by grinding in the presence of CaO at room temperature. This method is simple, efficient, economical, and environmentally benign.

Abstract

Synth. Commun. 2004, 34, 2053

Three‐Component Synthesis of 3‐Aminomethylene‐thiochroman‐2,4‐diones from 4‐Hydroxycoumarin

Hyun‐Ja Park and Kee‐In Lee*

Bio‐Organic Science Division, Korea Research Institute of Chemical Technology, Yusong, Taejon, Korea

A three‐component synthesis of 3‐aminomethylene‐thiochroman‐2,4‐dione derivatives 2–22 by the condensation reactions of amines, α‐aminoacids, ureas, and carbamates with 4‐hydroxythiocoumarin 1, respectively, in the presence of triethyl orthofomate is described.

Abstract

Synth. Commun. 2004, 34, 2063

Pd(II)‐Catalyzed Synthesis of Unsymmetrical Biaryls from Tetraphenylborate and Aryl Halides Under Microwave Activation

Jin‐Xian Wang,* Yihua Yang, and Bangguo Wei

Department of Chemistry, Institute of Chemistry, Northwest Normal University, Lanzhou, P.R. China

A palladium‐catalyzed cross‐coupling reaction of sodium tetraphenylborate 1 with aryl halides 2a–j using KF/Al₂O₃ as supported reagents under microwave irradiation conditions gives the unsymmetrical biaryls 3a–j in good yields.

Abstract

Synth. Commun. 2004, 34, 2071

Solid Supported Microwave‐Assisted Beckmann Rearrangement of Ketoximes in Dry Media

Firouz Matloubi Moghaddam,* Abbas Ali Rastegar Rad, and Hassan Zali‐Boinee

Department of Chemistry, Sharif University of Technology, Tehran, Iran

Abstract

Synth. Commun. 2004, 34, 2077

Synthesis of an Amino Acid With Protected Cyclen Side Chain Functionality

Stefan Miltschitzky and Burkhard König*

Institut für Organische Chemie, Universität Regensburg, Regensburg, Germany

The synthesis of a protected dipeptide with side chain functionality is reported.

Abstract

Synth. Commun. 2004, 34, 2085

An Improved Greener Esterification of Fatty Alcohols Using a Renewable Acid–Ionic Liquid Couple as Catalyst‐Solvent

H.‐P.Nguyen,* S. Znifeche, and M. Baboulène

Laboratoire des Interactions Moléculaires et Réactivité Chimique et Photochimique, UMR (CNRS) 5623, Université Paul Sabatier, Toulouse, France

A simple and efficient method was described for the esterification of various organic acids with C4 to C18 alcohols using the 1‐octyl 3‐methyl imidazolium tetrafluoroborate — p‐toluenesulfonic acid (OMIM/BF₄ PTSA) couple, without organic solvent, either by classic heating or by microwave irradiation.

The notable features of this procedure are mild reaction conditions, simplicity in operation, improved yields, cleaner reaction and recyclability of couple.

Abstract

Synth. Commun. 2004, 34, 2095

Facile Preparation of Benzylic Iodides under Solvent‐Free Conditions Using Microwave Irradiation

Jong Chan Lee,* Jin Young Park, and Eun Sang Yoo

Department of Chemistry, Chung‐Ang University, Seoul, South Korea

A new and efficient method for the conversion of benzylic alcohols into benzylic iodides is described.

Abstract

Synth. Commun. 2004, 34, 2101

Microwave‐Assisted Elimination Reaction of trans‐4‐(4‐Fluorophenyl)‐3‐chloromethyl‐1‐Methylpiperidine on Alumina

Hana Navrátilová,^1,* Zdeněk Kříž,² and Milan Potáček

¹Department of Organic Chemistry and ²National Centre for Biomolecular Research, Faculty of Science, Masaryk University, Brno, Czech Republic, Brno, Czech Republic

Microwave irradiation of trans‐4‐(4‐fluorophenyl)‐3‐chloromethyl‐1‐methylpiperidine on alumina or KF‐alumina under solvent‐free conditions provided the elimination product which isomerized to 4‐(4‐fluorophenyl)‐1,5‐dimethyl‐1,2,5,6‐tetrahydropyridine. The effect of alumina and irradiation time on reaction conversion and the extent of isomerization was examined.

Abstract

Synth. Commun. 2004, 34, 2117

Solvent‐Free Reactions of Fullerenes with Diethyl Bromomalonate in the Presence of Various Inorganic Bases Under High‐Speed Vibration Milling

Ru‐Fang Peng,1 Guan‐Wu Wang,^1,2,* Ye‐Bing Shen,¹ Yu‐Jin Li,^1,2 Ting‐Hu Zhang,¹ You‐Cheng Liu,^1,2 Yasujiro Murata³ and Koichi Komatsu³

¹Department of Chemistry, University of Science and Technology of China, Hefei, Anhui, P. R. China.

²National Laboratory of Applied Chemistry, Lanzhou University, Lanzhou, Gansu, P. R. China

³Institute for Chemical Research, Kyoto University, Uji, Kyoto, Japan