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 Maiti21Pfizer Global Research and Development, Department of Chemistry, Ann Arbor, Michigan, USA; 2Naeja Pharmaceuticals, Inc., Department of Chemistry, Edmonton, Alberta, Canada 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 Gao21Department 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. 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. 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. Synth. Commun.2003, 33, 3497 Convenient Synthesis of 5,6,7,8-Tetrahydroquinolin-8-Ylamine and 6,7-Dihydro-5H -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. 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 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. Synth. Commun.2003, 33, 3519 New Synthesis of Thymidylate Synthase Inhibitor Raltitrexed Sheng-Li Cao,1,* Rong Wan,2 and Yu-Ping Feng21Department 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. 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. Synth. Commun.2003, 33, 3537 Facile Synthesis of 2H-1,4-Benzothiazin-3(4H)-ketoximes and 2H-1,4-Benzoselenazin-3(4H)-ketoximes Promoted by SmI2 Xiaoliang Xu1 and Yongmin Zhang1,2,* 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. 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. 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 Zhang1,2,* 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 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. 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. 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 Zhang1,2,* 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 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. 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. Synth. Commun.2003, 33, 3597 The Ester and Amide Derivatives of 4-(4-Methyl Piperazino-methyl) Benzoic Acid P. Sairam1,* Ramachandra Puranik,1 Avijit. S. Kelkar,1 S. Sasikiran,1 M. Veerender,1and A. Parvathi21Dr. 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. 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. 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. 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. 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. 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. Collard1,* 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 [ABSTRACT FROM AUTHOR]