Graphical Abstracts

Abstract

Synth. Commun. 2003, 33, 3467

An Expeditious Synthesis of 6-Alkyl-5-(4′-aminophenyl)-pyrimidine-2,4-diamines

Daniel D. Holsworth,^1,* Michael Stier,¹ Jeremy J. Edmunds,¹ Wei He,² Samuel Place,² and Samarendra Maiti²

¹Pfizer Global Research and Development, Department of Chemistry, Ann Arbor, Michigan, USA; ²Naeja Pharmaceuticals, Inc., Department of Chemistry, Edmonton, Alberta, Canada

Abstract

Synth. Commun. 2003, 33, 3477

The Convenient Synthesis of Amphiphilic Phenanthroline Derivatives

Zu-Qian Bian,¹ Ke-Zhi Wang,^1,* Lin-Pei Jin,¹ and Li-Hua Gao²

¹Department of Chemistry, Beijing Normal University, Beijing, P.R. China; ²School of Chemical and Environmental Engineering, Beijing Technology and Business University, Beijing, P.R. China

The convenient synthesis of three amphiphilic phenanthroline derivatives is described.

Abstract

Synth. Commun. 2003, 33, 3483

Nitrogen Heterocyclic Bases as Catalysts for the Selective Synthesis of Symmetric P,P′-Disubstituted Bisphosphonate Esters

Dominique C. Stepinski, Jacob N. Hess, and Albert W. Herlinger*

Department of Chemistry, Loyola University Chicago, Chicago, Illinois, USA

Nitrogen heterocyclic bases were investigated as potential catalysts for the selective synthesis of symmetric P,P′-disubstituted partial esters of methylenebisphosphonic acid.

Abstract

Synth. Commun. 2003, 33, 3491

PTC Sulfanylation of Arylacetates

Liliana Marzorati,* Marco Antonio da Silva, Blanka Wladislaw, and Claudio Di Vitta

Instituto de Química, Universidade de São Paulo, São Paulo, S.P., Brazil

Sulfanylation of six arylacetates was performed under solvent-free PTC conditions.

Abstract

Synth. Commun. 2003, 33, 3497

Convenient Synthesis of 5,6,7,8-Tetrahydroquinolin-8-Ylamine and 6,7-Dihydro-5 H -Quinolin-8-One

E. J. McEachern,* Wen Yang, Gang Chen, Renato T. Skerlj, and Gary J. Bridger

AnorMED Inc., Langley, British Columbia, Canada

A novel two-step synthesis of 5,6,7,8-tetrahydroquinolin-8-ylamine, involving regioselective nitrosation of 5,6,7,8-tetrahydroquinoline followed by oxime reduction, is described. Oxime hydrolysis affords 6,7-dihydro-5H-quinolin-8-one.

Abstract

Synth. Commun. 2003, 33, 3503

tris (2-Carboxyethyl)Phosphine (TCEP) for the Reduction of Sulfoxides, Sulfonylchlorides, N -Oxides, and Azides

Anne-Marie Faucher* and Chantal Grand-Maître

Boehringer Ingelheim (Canada) Ltd., Research and Development, Laval (Québec), Canada

Abstract

Synth. Commun. 2003, 33, 3513

A Novel and Efficient Strategy for the Preparation of 2,4-Disubstituted-1,2,3-triazoles

Yun Luo and Yongzhou Hu*

Department of Medicinal Chemistry, School of Pharmaceutical Science, Zhejiang University, Hangzhou, P.R. China

We have developed a novel and efficient method for the preparation of 2,4-disubstituted-1,2,3-triazoles. These compounds 3a–3p were synthesized in good yield by refluxing α-aminoacetophenones and hydrazines in glacial acetic acid. The reaction proceeds under mild conditions and is compatible with various functional groups.

Abstract

Synth. Commun. 2003, 33, 3519

New Synthesis of Thymidylate Synthase Inhibitor Raltitrexed

Sheng-Li Cao,^1,* Rong Wan,² and Yu-Ping Feng²

¹Department of Chemistry, Capital Normal University, Beijing, P.R. China; ²Department of Chemistry, Tsinghua University, Beijing, P.R. China

A new synthetic route was elaborated to yield thymidylate synthase inhibitor Raltitrexed using 2,5-thiophenedicarboxylic acid as starting material via 6 steps in 18.2% overall yield.

Abstract

Synth. Commun. 2003, 33, 3527

Studies on Flavans. III. The Total Synthesis of (±)-7,4′-Dihydroxy-3′-methoxyflavan, (±)-7,3′-Dihydroxy-4′-methoxyflavan, and (±)-7,4′-Dihydroxyflavan

Jijun Xue, Xianshu Zhang, Xuesong Chen, Yingpeng Zhang, and Ying Li*

National Laboratory of Applied Organic Chemistry and Institute of Organic Chemistry, Lanzhou University, Lanzhou, Gansu, People's Republic of China

The first total synthesis of (±)-7,3′-dihydroxy-4′-methoxyflavan (1) and (±)-7,4′-dihydroxy-3′-methoxyflavan (2), along with the synthesis of (±)-7,4′-dihydroxyflavan (3), three naturally occurring flavans, were described. The key step is the cyclization of 1,3-diaryl-1-propanol by BF₃·Et₂O.

Abstract

Synth. Commun. 2003, 33, 3537

Facile Synthesis of 2 H -1,4-Benzothiazin-3(4H)-ketoximes and 2 H -1,4-Benzoselenazin-3(4 H )-ketoximes Promoted by SmI₂

Xiaoliang Xu¹ and Yongmin Zhang^1,2,*

¹Department of Chemistry, Zhejiang University (Campus Xixi), Hangzhou, P.R. China; ²State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, Shanghai, P.R. China

2H-1,4-Benzothiazin-3(4H)-ketoximes and 2H-1,4-benzoselenazin-3(4H)-ketoximes were synthesized by the reductive cyclization of bis(o-nitrophenyl) disulfides or diselenides with aromatic or aliphatic β-nitroethylenes using SmI₂ in moderate to good yields under mild conditions.

Abstract

Synth. Commun. 2003, 33, 3545

A Soluble Block Copolymer-Supported bis -Cinchona Alkaloid Ligand for the Asymmetric Dihydroxylation of Olefins

Yong-Qing Kuang, Sheng-Yong Zhang,* and Ling-Ling Wei

Department of Chemistry, Fourth Military Medical University Xi'an, China

A soluble block copolymer-supported ligand was prepared via polycondensation of a bis-cinchona alkaloid derivative, polyethylene glycol, and terephthaloyl chloride. Its application in the asymmetric dihydroxylation of olefins delivered very good enantioselectivity.

Abstract

Synth. Commun. 2003, 33, 3551

Samarium Diiodide Mediated Barbier-Type Reaction of 2-Chloromethylbenzoxazole and 2-Chloromethylbenzothiazole with Carbonyl Compounds: A Convenient Synthesis of 1-(β-Hydroxyalkyl)benzoxazoles and 1-(β-Hydroxyalkyl) Benzothiazoles

Xiaoliang Xu¹ and Yongmin Zhang^1,2,*

¹Department of Chemistry, Zhejiang University (Campus Xixi), Hangzhou, P.R. China; ²State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, Shanghai, P.R. China

Abstract

Synth. Commun. 2003, 33, 3561

Synthesis of Substituted 2-Alkoxycarbonyl or 2-Cyano-1,3-butadienes

Yu-Xiu Liu, Cheng-Fu Xu, Ru-Zhen Cao, and Lun-Zu Liu*

National Key Laboratory of Elemento-Organic Chemistry, Institute of Elemento-Organic Chemistry, Nankai University, Tianjin, China

A series of 2-butoxycarbonyl-1,4-diaryl-1,3-butadienes and 2-cyano-1,4-diaryl-1,3-butadienes are synthesized by one pot reaction of 2-butoxycarbonyl or 2-cyanoethenylphosphonate with aromatic aldehyde and tributylphosphine.

Abstract

Synth. Commun. 2003, 33, 3567

PEG-Supported Liquid-Phase Parallel Synthesis of Phenyloxyacetyl Thioureas

Zheng Li, Junke Wang, and Xicun Wang*

College of Chemistry and Chemical Engineering, Northwest Normal University, Gansu, Lanzhou, P.R. China

An efficient PEG-supported liquid-phase parallel synthesis of phenyloxyacetyl thioureas is described.

Abstract

Synth. Commun. 2003, 33, 3575

Substitution of the BenzotriazoLyl Group in N -(α-Amidoalkyl)benzotriazoles and N -(α-Sulfonamidoalkyl)benzotriazoles with Allylsamarium Bromide

Xiaoxia Wang,¹ Jian Li,¹ and Yongmin Zhang^1,2,*

¹Department of Chemistry, Zhejiang University (Campus Xixi), Hangzhou, P.R. China; ²State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, Shanghai, P.R. China

Abstract

Synth. Commun. 2003, 33, 3583

Ruthenium-Catalyzed Coupling Reaction of Benzylic Halides

Yanjun Li* and Taeko Izumi

Department of Chemistry and Chemical Engineering, Faculty of Engineering, Yamagata University, Yonezawa, Japan

Reported herein is a novel method on dechlorination coupling reaction of halides by using RuCl₂(PPh₃)₃ catalyst under a hydrogen atmosphere with benzene as the solvent, which affords alkanes in excellent yields.

Abstract

Synth. Commun. 2003, 33, 3589

Robinson's Annelation: Synthesis of Sydnone-Containing 3′-Arylcyclohexenone Derivatives Under Solvent Free Conditions

Balakrishna Kalluraya* and Ganesha Rai

Department of Studies in Chemistry, Mangalore University, Mangalagangothri, Karnataka, India

An eco-friendly solvent free method for Robinson's annelation is described.

Abstract

Synth. Commun. 2003, 33, 3597

The Ester and Amide Derivatives of 4-(4-Methyl Piperazino-methyl) Benzoic Acid

P. Sairam^1,* Ramachandra Puranik,¹ Avijit. S. Kelkar,¹ S. Sasikiran,¹ M. Veerender,¹and A. Parvathi²

¹Dr. Reddy's Laboratories Ltd., IDA Bolaram, Hyderabad, A. P., India; ²Aurangabad College for Women, Maratwada University, Aurangabad, Maharastra, India

Synthesis of 4-(4-methyl piperazinomethyl) benzoic acid (1) from a commercially available and inexpensive starting material with enhanced yields. This acid (1) is then further used for the synthesis of the ester and amide.

Abstract

Synth. Commun. 2003, 33, 3607

Copper (I) Chloride Catalyzed Synthesis of Diaryl Ethers in Ionic Liquids Under Mild Conditions

S. M. S. Chauhan,* Nidhi Jain, Anil Kumar, and K. A. Srinivas

Department of Chemistry, University of Delhi, Delhi, India

The reaction of different aryl halides with aryl oxides catalyzed by CuCl in 1-butyl-3-methyl-imidazolium tetrafluoroborate [bmim][BF₄] and 1-butyl-3-methyl-imidazolium hexafluorophosphate [bmim][PF₆] ionic liquids to give diaryl ethers in 54–90% yields has been studied under mild reaction conditions.

Abstract

Synth. Commun. 2003, 33, 3615

An Expedient Synthesis of Allylic/Secondary Bromides From Dehydration of Tertiary-β-Bromo Alcohols

B. K. Bettadaiah and P. Srinivas*

Plantation Products, Spices and Flavour Technology Department, Central Food Technological Research Institute, Mysore, India

Tertiary-β-bromo alcohols, derived from simple monoterpenes and olefins, react with BF₃·OEt₂ in refluxing benzene in 1–2 h to afford the corresponding allylic/secondary bromides in 45–90% yield. In case of substrates containing olefinic or hydroxyl groups, formation of cyclic ethers was observed.

Abstract

Synth. Commun. 2003, 33, 3621

N -Iodosuccinimide: an Efficient Reagent for Regioselective Heterocyclization of 3-Allyl-4-hydroxy[1]benzopyran-2-ones

K. C. Majumdar,* P. K. Basu, and B. Roy

Department of Chemistry, University of Kalyani, Kalyani, West Bengal, India

Thermal Claisen rearrangement of 4-allyloxy[1]benzopyran-2-ones in refluxing chlorobenzene gave 3-allyl-4-hydroxy[1]benzopyran-2-ones in 82–90% yield. A number of 3-iodopyrano[3,2-c][1]benzopyran-5(2H)-ones were synthesized in 80–92% yield by the regioselective heterocyclization of 3-allyl-4-hydroxy[1]benzopyran-2-ones with N-iodosuccinimide in acetonitrile at 0–5°C.

Abstract

Synth. Commun. 2003, 33, 3631

Efficient Route to the Pineal Hormone Melatonin by Radical-Based Indole Synthesis

Douglas W. Thomson, Aurélien G. J. Commeureuc, Stefan Berlin, and John A. Murphy*

Department of Pure and Applied Chemistry, University of Strathclyde, Glasgow, UK

The hormone melatonin, which is known to have a range of important biological effects, has been prepared in a high-yielding route that features formation of the indole nucleus by radical cyclization. Mediation of the radical cyclization by tristrimethylsilylsilane (TTMSS) is more efficient than by N-ethylpiperidine hypophosphite.

Abstract

Synth. Commun. 2003, 33, 3643

The One-Pot Synthesis and Diels-Alder Reactivity of 2,5-Dihydrothiophene-1,1-Dioxide-3-Carboxylic Acid

Genara S. Andrade,¹ Joachim E. Berkner,¹ Charles L. Liotta,¹ Charles Eckert,² David A. Schiraldi,³ Arthur Andersen,⁴ and David M. Collard^1,*

¹School of Chemistry and Biochemistry, Georgia Institute of Technology, Atlanta, Georgia, USA; ²School of Chemical Engineering, Georgia Institute of Technology, Atlanta, Georgia, USA; ³KoSa, Spartanburg, South Carolina, USA; ⁴DuPont, Experimental Station, Wilmington, Deleware, USA