Letters in Organic Chemistry

ISSN: 1570-1786

Letters in Organic Chemistry
Volume 3, Number 12, December 2006


Synthesis and Functionalization of 6,7-Dihydro-[1,4]Dioxino[2,3-d] Pyrimidines Pp. 877-881
Guido Lavecchia, Sabine Berteina-Raboin & Gérald Guillaumet



The cyclization of 4,5-dihydroxy-2-methyl-pyrimidine followed by dibromination and oxidation of the methyl group led to 6,7-dihydro-[1,4]dioxino[2,3-d]pyrimidine-2-carboxaldehyde. This compound underwent subsequent chemical transformations on carbonyl group to synthesize various 2-substituted-6,7-dihydro-[1,4]dioxino[2,3-d]pyrimidines.

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Synthesis of Pseudopeptides Derived from (R,R)-Tartaric Acid as Potential Inhibitors of HIV-Protease Pp. 882-886
José C. Barros, Joaquim F.M. da Silva, Alexandre R. Calazans, Amilcar Tanuri, Rodrigo de Morais Brindeiro, John S. Williamson, Octavio A.C. Antunes



New pseudopeptides possessing C2 symmetry and dihydroxyethylene core derived from (R,R)-tartaric acid and amino esters have been synthesized as potential inhibitors of HIV protease. The amino esters were chosen in order to interact with P1/P1´ and P2/P2´ subsites of the enzyme. The products were obtained in good yields without noticeable racemization.

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A Facile One-Pot Synthesis of New Spiro Pyrrolidine-Oxindoles Under Ultrasonic Irradiation in DMSO-H2O Pp. 887-890
Javad Azizian, Ali Saffar-Teluri & Ali Asadi



Ultrasonic irradiation effectively promotes the 1,3-dipolar cycloaddition reaction of L-phenyl alanine and isatin derivatives with N-aryl maleimides in aqueous solution.
 

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Convenient Preparation of Original Vinylic Chlorides with Antiparasitic Potential in Quinoline Series Pp. 891-897
Pierre Verhaeghe, Pascal Rathelot, Sylvain Rault & Patrice Vanelle



The synthesis of various original vinylic chlorides from trichloromethylated substrates in the quinoline series is described herein. This reaction takes place under mild operating conditions via a monoelectronic transfer mechanism and presents elevated yields.

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Novel One-Pot Synthesis of Amide Derivatives of Methylenebisphosphonate Utilizing the Mesyl Moiety as Leaving Group Pp. 898-900
Jonna Jokiniemi, Markku Ahlgrén & Jouko J. Vepsäläinen



A simple and selective synthesis has been developed for the preparation of partial amide esters of (dichloromethylene)bisphosphonic acid from easily available tetramethyl ester.
 

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Regio- and Chemoselective Reduction of Aromatic Nitro and Carbonyl Compounds Over Novel Baker’s Yeast Immobilized Nanoporous Silicates Pp. 901-904
Susanta K. Mohapatra & Parsuraman Selvam



Baker's yeast immobilized MCM-41 molecular sieves are found to be a highly efficient, heterogeneous catalyst for the reduction of aromatic nitro and carbonyl containing compounds under transfer hydrogenation conditions.

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First Synthesis of a G-2 Melamine Dendrimer with Serinolic Peripheral Groups Pp. 905-910
Mircea Darabantu, Monica Pintea, Marijana Fazekas, Pedro Lameiras, Camelia Berghian, Isabelle Delhom, Ioan Silaghi-Dumitrescu, Nelly Plé & Alain Turck



Starting from (1S,2S)-2-amino-1-(4-nitrophenyl)-propane-1,3-diol (l-p-nitrophenylserinol), cyanuryl chloride and piperazine, the synthesis is described to occur in five linear (nine total) steps and 27% overall yield.
 

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Synthesis of Cholesterylated Carboxylic Acids with Oligo(Polyethylene Glycols) Units for Gene Delivery Pp. 911-914
Xiaochun Wu, Yong Wu, Li Hai & Ying Bao



A series of cholesterylated carboxylic acid with oligo(polyethylene glycols) units L1-L6 as the cell targeting ligands for gene delivery to hepatoma cells were synthesized from cholesteryl tosylate.

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Preparation of Heterocycles by Microwave-Induced Retro Diels-Alder Reaction Pp. 915-916
Ferenc Miklós, Géza Stájer & Ferenc Fülöp



The preparation of pyrimidinones and fused-ring heterocycles (pyrimidophthalazine and 1,3 oxazinoisoindole) is described.

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Synthesis of Dispiro [Flavanone/Chromanone/Tetralone]-Pyrrolo[1,2-a] Isoquinolinespiro [3.2´´]Acenaphthen-1´´-One Systems Through Three Component 1,3-Dipolar Cycloaddition Reaction Pp. 917-921
Jayadevan Jayashankaran, Rathna Durga R.S. Manian & Raghavachary Raghunathan



An efficient route for the synthesis of dispiro-isoquinoline derivatives has been developed by 1,3-dipolar cycloaddition reaction across the exocyclic double bond of various active dipolarophiles.

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Crotylation of (R)-2,3-Cyclohexylideneglyceraldehyde: A Simple Strategy for the Synthesis of Enantiopure anti-Alzheimer (R)-Arundic Acid Pp. 922-925
Dibakar Goswami & Angshuman Chattopadhyay



The title compound was synthesized by exploiting a product obtained diastereoselectively by crotylation of a glyceraldehydes derivative.

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The Allylic Oxidation of Ionone-Like Dienes by Nanoscale Copper Catalyst in Imidazolium Ionic Liquids Pp. 926-931
Min Yang, Qian-Rong Peng, Guang-Fu Song, Jing-Bo Lan, Dong-Shan Wang, Jing-Song You & Ru-Gang Xie



The allylic oxidation of ionone-like dienes was investigated with copper salts and 70% aqueous tert-butyl hydroperoxide in imidazolium ionic liquids. TEM measurements showed the shape and size of dispersed Cu nanoparticles catalyst in our system.

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Convenient Per-O-Acetylation of Monosaccharides with Vinyl Acetate/ Na3PO4-H2O Pp. 932-935
Chun-juan Shi, Jianbo Zhang, Jie Fu & Jie Tang



Several monosaccharides were peracetylated in excellent isolated yields (89–100%) with vinyl acetate in aqueous Na3PO4. The per-O-acetylation reaction is fast and mild, as well as insensitive to water. Meanwhile, the workup is convenient and the catalyst can be recycled easily.

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Hexamethylenetetramine-Ionic Liquids Catalyzed Baylis-Hillman Reactions Pp. 936-939
Rodrigo O.M.A. de Souza, Pedro H. Fregadolli, Karen M. Gonçalves, Lucia C. Sequeira, Vera L.P. Pereira, Lúcio C. Filho, Pierre M. Esteves, Mário L.A.A. Vasconcellos, Octavio A.C. Antunes



In the present paper it is described the use of HMT combined to the use of bmim+ type ionic liquids as cheap, friendly and efficient catalytic systems for Baylis-Hillman reactions between aromatic aldehydes and acrylonitrile or methyl acrylate. The BH adducts were obtained in moderate to good yields, in short reaction times. The ionic liquid can be recycled.

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An Expedient Approach to the Synthesis of Chloroacetic, Dichloroacetic and Acetic Acid Catalyzed by Sulfuric Acid in the Presence of Crown Ethers Pp. 940-942
Shahnaz Perveen, Tahira B. Sarfaraz, Khalid M. Khan & Wolfgang Voelter



Chloroacetic, dichloroacetic and acetic acid were prepared by direct transformation of trichloroethylene, tetrachloroethylene and 1,1-dichloroethylene, respectively, using sulfuric acid in the presence of catalytic amounts of crown ethers.

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Preparation of Arene Carboxylic Acids Via a Polymer-Supported Kröhnke Reaction Pp. 943-947
Gloria Brusotti, Jörg Habermann, Ornella Azzolina & Simona Collina



A synthesis of arene carboxylic acids from acetophenones using polymer-supported reagents and microwave-assisted chemistry has been developed.

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A Highly Efficient Low Temperature Modification of the Classical Ullmann Reaction Pp. 948-954
Frédéric R. Leroux, Roger Simon & Nathalie Nicod


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