Graphical Abstracts

Abstract Synth. Commun. 2004, 34, 4243 Sulfamic Acid as a Cost‐Effective and Recyclable Catalyst for Protection of Carbonyls to Acetals and Ketals Under Mild Conditions of Alcohols over Sulfamic Acid as Reusable Catalyst Weizhong Gong,1,2 Bo Wang,1 Yanglong Gu,1 Liang Yan,1 Liming Yang,1 and Jishuan Suo1,3 1State Key Laboratory for Oxo Synthesis and Selective Oxidation, Lanzhou Institute of Chemical Physics, Chinese Academy of Sciences, Lanzhou, China 2Institute of Biology of Gansu Academy 3Chengdu Organic Chemicals Co. Ltd., Chinese Academy of Sciences, China An efficient H2NSO3H‐catalyzed protection of various carbonyl compounds at room temperature was investigated. The features of mild conditions, cost‐efficient catalyst, simple workup, and the recyclability of the catalyst were represented in this process. Synth. Commun. 2004, 34, 4249 Ytterbium Triflate Catalyzed Friedel–Crafts Reaction: Facile Synthesis of Diaryl Ketones Weike Su and Can Jin College of Pharmaceutical Sciences, Zhejiang University of Technology, Hangzhou, P.R. China Friedel–Crafts reaction of aromatic compounds (benzenes, thiophene, furan, pyrrole, naphthalene and benzothiophene) with bis(trichloromethyl) carbonate [BTC] was efficiently catalyzed by ytterbium triflate [Yb(OTf)3] to give diaryl ketones with moderate to good yields. Synth. Commun. 2004, 34, 4257 One‐Pot Synthesis of Ene‐Lactams Via N‐Debenzylation of Keto‐Containing N‐2,4‐Dimethoxylbenzylamides Wai Ming Kan,1 Ching‐Lung Cheng,2 and Ching‐Yuh Chern2 1Department of Pharmacology, National Cheng Kung University, Tainan, Taiwan R.O.C. 2Department of Applied Chemistry, National Chiayi University, Chiayi, Taiwan, R.O.C. Synth. Commun. 2004, 34, 4265 An Efficient Procedure for the Synthesis of Benzimidazole Derivatives Using Yb(OTf)3 as Catalyst Under Solvent‐Free Conditions Limin Wang,1 Jia Sheng,1 He Tian,1 and Changtao Qian2 1Institute of Fine Chemicals, East China University of Science and Technology, Shanghai, P. R. China 2Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, Shanghai, P. R. China Synth. Commun. 2004, 34, 4273 Bromination of Azulene Derivatives with Sodium Monobromoisocyanurate Toshiaki Sumida,1 Shigeru Kikuchi,1 and Kimiaki Imafuku2 1Graduate School of Science and Technology, Kumamoto University, Kurokami, Kumamoto, Japan 2Department of Chemistry, Faculty of Science, Kumamoto University, Kurokami, Kumamoto, Japan Synth. Commun. 2004, 34, 4285 New Method for the Synthesis of 5‐Hydroxycamptothecin Derivatives Xungui He, Heyong Gao, Wei Lu, and Junchao Cai Shanghai Institute of Materia Medica, SIBS, Chinese Academy of Sciences, China A facile method for the hydroxylation at C‐ring of camptothecins is described. Synth. Commun. 2004, 34, 4293 Gallium Triiodide Catalyzed Organic Reaction: A Convenient Synthesis of α‐Amino Phosphonates Peipei Sun, Zhixin Hu, and Zhihao Huang College of Chemistry and Environmental Science, Nanjing Normal University, Nanjing, China Synth. Commun. 2004, 34, 4301 Direct Formation of 2,3,5‐Trichloropyridine and Its Nucleophilic Displacement Reactions in Ionic Liquid Ping Zhong,1 Huanan Hu,1,2 and Shengrong Guo1,2 1Department of Chemistry, Wenzhou Normal College, Wenzhou, P. R. China 2Department of Chemistry, Jiangxi noraml University, Nanchang, P. R. China The nucleophilic displacement reactions of heterocyclic compounds in ionic liquids afforded 2‐[4‐(3,5‐dihalopyridin‐2‐yloxy)‐phenoxy]‐propionates 5. R1 = Cl, or F; 5a: R2 = Cl, R3 = C2H5; 5b: R2 = F, R3 = C2H5; 5c: R2 = Cl, R3 = CH3; 5d: R2 = F, R3 = CH3; 5e: R2 = Cl, R3 = CH2C6H5; 5f: R2 = Cl, R3 = CH2COC6H5; 5g: R2 = Cl, R3 = CH2CO2C2H5; 5h: R2 = Cl, R3 = CH2 C≡CH. Synth. Commun. 2004, 34, 4313 Preparation and Stereochemistry of the Isopropylidene Derivatives of 1,2‐Dihydronaphtho[2,1‐b]Furan‐1,2‐Diol and 1,2,9,10‐Tetrahydronaphtho[2,1‐b:7,8‐b′]Difuran‐1,2,9,10‐Tetraol in Comparison with the Corresponding Acetyl Derivatives Makoto Yamaye,1 Yoshiko Motoyanagi,1 Aya Nakagawa,1 Sanae Kametani,1 Tetsutaro Yoshinaga,2 Namiko Cho (Toh),1 Xiaobo Fan,2 and Taketoshi Kito2 1Faculty of Engineering, Kyushu Kyoritsu University, 1‐8 Jiyugaoka, Yahatanishi, Kitakyushu, Japan 2Department of Applied Chemistry, Kyushu Institute of Technology, 1‐1 Sensuicho, Tobata, Kitakyushu, Japan Synth. Commun. 2004, 34, 4325 An Efficient and Selective Deprotecting Method for Methoxymethyl Ethers Yungui Peng,1 Changyun Ji,1 Yingchun Chen,2 Chengzhi Huang,1 and Yaozhong Jiang2 1The School of Chemistry and Chemical Engineering, Southwest Normal University, Beibei, Chongqing, China 2Chengdu Institute of Organic Chemistry, Chinese Academy of Sciences, Chengdu, China Methoxymethyl ethers were selectively deprotected to the corresponding phenols in high yields by CBr4 and PPh3 in aprotic solvent (ClCH2CH2Cl) under slightly thermal reaction conditions. Synth. Commun. 2004, 34, 4331 KF‐Alumina Catalyzed One‐Pot Synthesis of Pyrido[2,3‐d]Pyrimidine Derivatives Xiang‐shan Wang,1,2,3 Zhao‐sen Zeng,1 Da‐qing Shi,1,3 Xian‐yong Wei,2 and Zhi‐min Zong2 1Department of Chemistry, Xuzhou Normal University, Xuzhou Jiangsu, P. R. China 2School of Chemical Engineering, China University of Mining and Technology, Xuzhou Jiangsu, P. R. China 3The Key Laboratory of Biotechnology on Medical Plant, Xuzhou, Jiangsu, P. R. China A series of pyrido[2,3‐d]pyrimidine derivatives were synthesized by the reaction of arylaldehyde, malononitrile, and 4‐amino‐2,6‐dihydroxylpyrimidine in ethyl alcohol at 80°C catalyzed by KF‐Al2O3. Synth. Commun. 2004, 34, 4339 Pinacol Coupling of Aromatic Aldehydes and Ketones using TiCl3‐Al‐EtOH Under Ultrasound Irradiation Ji‐Tai Li, Zhi‐Ping Lin, Na Qi, and Tong‐Shuang Li College of Chemistry and Environmental Science, Hebei University; Key Laboratory of Analytical Science and Technology of Hebei Province, Baoding, P. R. China Titanium trichloride in EtOH can be reduced by Al to the corresponding low‐valent titanium complexes. This can reduce some aromatic aldehydes and ketones to the corresponding pinacols in 40–82% yields within 30–90 min at r.t. under ultrasound irradiation. Synth. Commun. 2004, 34, 4349 Synthesis of Substituted 1,4‐Dihydropyridines in Water Using Phase‐Transfer Catalyst Under Microwave Irradiation Hojatollah Salehi1,2 and Qing‐Xiang Guo1 1Department of Chemistry, University of Science and Technology of China, Hefei, China 2Ministry of Science, Research and Technology, Tehran, Iran The synthesis of various substituted 1,4‐dihydropyridines has been achieved by the reaction of aldehydes, ethyl/methyl acetoacetates, and ammonium acetate in water using phase‐transfer catalyst under microwave irradiation. Compared to the classical Hantzsch reaction conditions, this new method consistently has the advantage of good yields and short reaction times. Bifunctional compounds containing two units have been synthesized using dialdehyde as precursor in good yields. Synth. Commun. 2004, 34, 4359 Synthesis of Some Novel Fluorinated Pyrazolo[3,4‐b]Pyridines S. P. Singh,1 Rajesh Naithani,2 Ranjana Aggarwal,1 and Om Prakash1 1Department of Chemistry, University of Kurukshetra, Kurukshetra, Haryana, India 2Department of Chemistry, University of Illinois at Chicago, Chicago, Illinois, USA A one‐pot procedure for synthesis of title compounds in good yield from α‐cyanoacetophenones is described. Synth. Commun. 2004, 34, 4369 Preparation of 3,17‐ and 3,20‐Difluoro‐Derivatives of the Androst‐5‐ene and Pregn‐5‐ene Series Richard A. Decréau and Charles M. Marson Christopher Ingold Laboratories, Department of Chemistry, University College London, London, UK Synth. Commun. 2004, 34, 4387 Ring Opening of 3‐Bromo‐2‐Isoxazolines to β‐Hydroxy Nitriles Martin G. Kociolek and Kyle P. Kalbarczyk Penn State Erie, The Behrend College, School of Science, Erie, PA, USA Synth. Commun. 2004, 34, 4395 Solvent‐Free Stereoselective Synthesis of cis‐1‐Carbomethoxy‐ 2‐Aryl‐3,3‐Dicyanocyclopropanes by Grinding Zhongjiao Ren,1 Weiguo Cao,1,2 Weiyu Ding,1 and Wen Shi1 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 The novel route of high stereoselective synthesis of cis‐1‐carbomethoxy‐2‐aryl‐3,3‐dicyanocyclopropanes by grinding is described. This process is simple, efficient, and environmentally benign. Synth. Commun. 2004, 34, 4401 Lutetium Triflate as an Efficient and Recyclable Catalyst for Chemoselective Thioacetalization of Aldehydes Surya Kanta De Department of Medicinal Chemistry and Molecular Pharmacology, School of Pharmacy, Purdue Cancer Center, Purdue University, West Lafayette, IN, USA Synth. Commun. 2004, 34, 4409 VO(acac)2 Catalyzed Oxidative Deprotection of Oximes, Hydrazones, and Semicarbazones Surya Kanta De Department of Medicinal Chemistry and Molecular Pharmacology, School of Pharmacy, Purdue Cancer Center, Purdue University, West Lafayette, IN, USA Synth. Commun. 2004, 34, 4417 Synthesis of [3H] dapsone Judith A. Egan, Scot Pounds and Crist N. Filer* PerkinElmer Life and Analytical Sciences Inc., 549 Albany St. Boston, Massachusetts 02118, USA An efficient synthesis of [3H] dapsone is described. Synth. Commun. 2004, 34, 4421 Synthesis of 4‐(R)‐Naphthalene‐2‐Yloxy‐1‐(1‐Phenyl‐(S)‐Ethyl)‐Pyrrolidin‐3‐(R)‐OL and 4‐(S)‐Naphthalen‐2‐Yloxy‐1‐(1‐Phenyl‐(S)‐Ethyl)‐Pyrrolidin‐3‐(S)‐OL: Versatile Chiral Intermediates for Synthesis Daniel D. Holsworth,1 Michael Stier,1 Wei Wang,2 Jeremy J. Edmunds,1 Tingsheng Li,3 and Samarendra N. Maiti3 1Department of Chemistry and Discovery Technologies,Pfizer Global Research and Development, Ann Arbor, MI, USA 2Department of Chemistry, Naeja Pharmaceutical, Inc., Edmonton, Alberta T6E 5V2, Canada A convenient and rapid synthesis of 4‐(R)‐(naphthalen‐2‐yloxy)‐1‐(1‐phenyl‐(S)‐ethyl)‐pyrrolidin‐3‐(R)‐ol (Compound 1) and 4‐(S)‐(naphthalen‐2‐yloxy)‐1‐(1‐phenyl‐(S)‐ethyl)‐pyrrolidin‐3‐(S)‐ol (Compound 2) is disclosed. The reaction scheme is highlighted by the meso‐epoxidation of 1‐(1‐phenyl‐(S)‐ethyl)‐2,5‐dihydro‐1H‐pyrrole followed by addition of 2‐naphthol alkoxide to provide both expected diastereoisomers. Separation of the diastereoisomers by crystallization provided access to both diastereoisomers in modest yield without the employment of expensive chiral catalysts. An x‐ray structure of Compound 1 was obtained to unambiguous assign the stereochemistry. These chiral pyrrolidine analogs should be useful as intermediates in natural product, combinatorial/parallel synthesis, and medicinal chemistry. Synth. Commun. 2004, 34, 4431 Efficient and Convenient Method for the Synthesis of Poly Functionalised 4H‐Pyrans B. P. V. Lingaiah, G. Venkat Reddy, T. Yakaiah, B. Narsaiah, S. N. Reddy, R. Yadla, and P. Shanthan Rao Fluoroorganics Division, Indian Institute of Chemical Technology, Hyderabad, India

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