Graphical Abstracts

Abstract

Synth. Commun. 2003, 33, 863

Modified Clays as Efficient Acid–Base Catalyst Systems for Diazotization and Diazocoupling Reactions

Damodaran Bahulayan,* Litka John, and Malathy Lalithambika

Clays and Clay Minerals Division, Regional Research Laboratory (CSIR), Kerala 695 019, India

An efficient and green route for the Diazotization and Diazocoupling reactions by making use of the bifunctional catalytic properties of modified clays and reported.

Abstract

Synth. Commun. 2003, 33, 871

Deprotection of Trimethylsilyl and Tetrahydropyranyl Ethers and of Ethylene Acetals with Tetramethylammonium Chlorochromate

Abdol R. Hajipour^1,2,* and Arnold E. Ruoho¹

¹Department of Pharmacology, University of Wisconsin Medical School, 1300 University Avernue, Madison, WI, 53706 1532, USA, ²Pharmaceutical Research Laboratory, College of Chemistry, Isfahan University of Technology, Isfahan 84156, IR, Iran

This paper describes oxidative deprotection of trimethylsilyl and tetrahydropyranyl ethers or ethylene acetals and ketals to the corresponding carbonyl compounds.

Abstract

Synth. Commun. 2003, 33, 879

A Facile Deprotection of Dithioacetals by FeCl₃/KI

Subhash P. Chavan,* Priti B. Soni, Ramesh R. Kale, and K. Pasupathy

Division of Organic Chemistry: Technology, National Chemical Laboratory, Pune 411008, India

Carbonyl compounds were regenerated from corresponding dithioacetals via refluxing with FeCl₃/KI and methanol as a solvent.

Abstract

Synth. Commun. 2003, 33, 885

Synthesis of Novel 7α-Thiol-bridged Progesterone Derivatives

James H. Wynne,* Christopher T. Lloyd, and George W. Mushrush

Naval Research Laboratory, Chemistry Division, 4555 Overlook Ave., SW, Code 6125, Washington, DC 20375, USA

The development of a convenient method for the preparation of novel highly functionalized 7α-thiol-bridged progesterones in three simple steps from progesterone is reported.

Abstract

Synth. Commun. 2003, 33, 895

Phenyl Sulphonyl Acetaldehyde Diethyl Acetal: A New Robust 1,2-Diol Protective Group

S. Chandrasekhar,* Ch. Srinivas, and P. Srihari

Indian Institute of Chemical Technology, Hyderabad-500007, India

A simple preparation of a novel resilient protective group for 1,2-diols is described herein which is remarkably stable in the presence of extremely harsh basic conditions as well as acidic media. The title reagent's versatility is detailed with numerous examples.

Abstract

Synth. Commun. 2003, 33, 903

Thermal and Catalytic Reactions of Diazoacetylmetallocenes with [60]Fullerene

Roberto Pellicciari,¹ Benedetto Natalini,^1,* Tatiana V. Potolokova (nee Mukha),² Maura Marinozzi,¹ Marina N. Nefedova,² Alexander S. Peregudov,² and Viatcheslav I. Sokolov²

Università di Perugia, Dipartimento di Chimica e Tecnologia del Farmaco, Via del Liceo, 1-06123 Perugia, Italy, ²Institute of Organoelement Compounds, Russian Academy of Sciences 28, Vavilov Street, 117813 Moscow, Russia

Diazoacetyl derivatives of ferrocene (2) and cymantrene (4) were submitted to thermal and dirhodium(II)tetraacetate catalyzed reactions with [60]fullerene (1) thus affording the methanofullerenes 3a and 6, the fulleroids 3b and 3c, and the dihydrofuranofullerene 5.

Abstract

Synth. Commun. 2003, 33, 915

New, Scalable Route for the Synthesis of a Trans-Fused Hexahydro-1H-Phenanthren-2-One from a Conjugated Tetrahydro-3H-Phenanthren-2-One

Bradley P. Morgan,* Richard V. Trilles, and Graeme F. Woodworth

Pfizer Global Research and Development, Pfizer Inc., Groton, Connecticut 06371, USA

A three-step, readily scalable route for the conversion of a ring-conjugated tetrahydro-3H-phenanthren-2-one to a trans-fused hexahydro-1H-phenanthren-2-one is described. The key step is the hydrogenation of a double bond using a nearby ketal moiety to assist in the stereoselective delivery of the hydrogen.

Abstract

Synth. Commun. 2003, 33, 921

The Use of Ultrasound in the Synthesis of 2-Carboxy Substituted Diphenylethers Using Water as Solvent

Rolando F. Pellón Comdom* and Maite L. Docampo Palacios

Center of Pharmaceutical Chemistry, P.O. Box 16042, Havana, Cuba

An improved synthesis of 2-carboxy substituted diphenylethers using water as solvent can be achieved by ultrasound irradiation.

Abstract

Synth. Commun. 2003, 33, 927

Synthesis of 1-(N-Alkylidene or Benzylideneamino)-1,6-dihydro -2-Methylthio-6-oxo-pyrimidine from Meldrum's Acid Derivatives

Xian Huang* and Zhanxiang Liu

Department of Chemistry, Zhejiang University (Campus Xixi), Hangzhou, 310028, P. R. China

Abstract

Synth. Commun. 2003, 33, 935

A Green Preparation of N-Chloro- and N-Bromosaccharin

Soraia P. L. de Souza, Joaquim F. M. da Silva, and Marcio C. S. de Mattos*

Instituto de Química, Departamento de Química Orgânica, Universidade Federal do Rio de Janeiro, Caixa Postal 68545, 21945-970, Rio de Janeiro, Brazil

Abstract

Synth. Commun. 2003, 33, 941

A Convenient Procedure for the Synthesis of O⁶-Benzylguanine Derivatives by Phase Transfer Catalysis

Xuan Liu,¹ Qi-Huang Zheng,^1,* Gary D. Hutchins,¹ Xiangshu Fei,¹ Leonard C. Erickson,³ Kathy D. Miller,² Bruce H. Mock,¹ Barbara E. Glick-Wilson,¹ Wendy L. Winkle,¹ K. Lee Stone,¹ and Kathy A. Carlson¹

Departments of ¹Radiology, ²Medicine, and ³Pharmacology and Toxicology, Indiana University School of Medicine, Indianapolis, IN 46202, USA

O⁶-Benzylguanine and its hydroxymethyl-, halo-, methoxy-, and methyl-substituted derivatives have been synthesized by a convenient procedure using phase transfer catalysis.

Abstract

Synth. Commun. 2003, 33, 953

A Convenient and Inexpensive Method for Conversion of Thiocarbonyl Compounds to their Oxo Derivatives Using Oxone Under Solvent-Free Conditions

Iraj Mohammadpoor-Baltork,* Majid M. Sadeghi, and Karim Esmayilpour

Department of Chemistry, Isfahan Univeristy, Isfahan 81744, Iran

A rapid, convenient and inexpensive method for the conversion of thiomides, thioureas and thioesters to their carbonyl compounds using oxone under solvent-free conditions is reported.

Abstract

Synth. Commun. 2003, 33, 961

Regio-Selective Mono Nitration of Phenols with Ferric Nitrate in Room Temperature Ionic Liquid

R. Rajagopal and K. V. Srinivasan*

Division of Organic Chemistry: Technology, National Chemical Laboratory, Pune-411 008, Maharashtra, India

The mono nitration of phenols were synthesized in excellent isolated yields with notably high para selectivities by nitration of phenols with ferric nitrate in the ionic liquid [bbim]BF₄.

Abstract

Synth. Commun. 2003, 33, 967

Synthesis of Aryl-Substituted 1,3-Butadiones

Burkhard König*

Institut für Organische Chemie, Universität Regensburg, D-93040 Regensburg, Germany

Several 1,3-butadiones bearing electron rich arenes have been prepared from the corresponding esters and lithiated imines. The formation of scandium(III) complexes illustrate their ligand ability.

Abstract

Synth. Commun. 2003, 33, 977

Preparation and Characterization of Methyl Substituted 2,2′-Dipyridyl Diselenides, 2,2′-dipyridyl-Ditellurides, and Their Derivatives

K. K. Bhasin,^1,* V. K. Jain,² H. Kumar,¹ Shweta Sharma,¹ S. K. Mehta,¹ and Jaspreet Singh¹

Department of Chemistry and Centre of Advanced Studies in Chemistry, Panjab University, Chandigarh-160014, India, ²Novel Materials and Structural Chemistry Division, Bhabha Atomic Research Centre, Mumbai-400085, India

A number of methyl substituted 2,2′-dipyridyl diselenides and -ditellurides 1 have been prepared. Effect of the solvent and the substituents on the rate of these reactions has been studied. 2-Methylseleno/telluro picolines 2 have been prepared through two routes.

Abstract

Synth. Commun. 2003, 33, 989

A Novel Uncatalyzed Insertion Reaction of In Situ Formed Trichlorosilyl Cyanide with Imines: A Facile Silicon Mediated Synthesis of α-Aminonitriles

Abdel-Aziz S. El-Ahl

Chemistry Department, Faculty of Science, Mansoura University, 35516 Mansoura, Egypt

The tetrachlorosilane-potassium cyanide reagent combination, (trichlorosilyl cyanide in situ) undergoes addition reaction onto saturated aldimines and a regiospecific 1,2-addition reaction onto α,β-unsaturated aldimines to give the corresponding α-aminonitriles in excellent yield, under exceedingly mild conditions, in absence of any catalyst.

Abstract

Synth. Commun. 2003, 33, 999

Regioselective Azidolysis of Epoxides Catalyzed with LiBF₄

F. Kazemi,* A. R. Kiasat, and S. Ebrahimi

Chemistry Department, College of Science, Shahid Chamran University, Ahvaz, Iran

Efficient and regioselective conversion of epoxiodes to vicinal azidoalcohols with sodium azide in wet t-butanol and in the presence of catalytic amount of lithium tetrafluoroborate, LiBF₄ in excellent yields under mild reaction conditions is described.

Abstract

Synth. Commun. 2003, 33, 1005

Synthesis of a Few bis-Binaphthol Derivatives

S. C. Jha and N. N. Joshi*

Division of Organic Synthesis, National Chemical Laboratory, Pune-411 008, India

A new family of bis-BINOL derivatives linked through ether group has been prepared.

Abstract

Synth. Commun. 2003, 33, 1011

A Two-Step Synthesis of Hexahydropyrrolo[1,2-d][1,2,4]Triazine-1,4-Dione and Related Compounds

Aleš Obreza¹ and Uroš Urleb^1,2*

University of Ljubljana, Faculty of Pharmacy, Aškerčeva 7, 1000 Ljubljana, Slovenia,

Lek d.d., Verovškova 57, 1000 Ljubljana, Slovenia

The synthesis of hitherto unknown heterocyclic compounds of type 1 by a new rapid two-step synthesis is described.

Abstract

Synth. Commun. 2003, 33, 1019

Synthesis of New Biosynthetically Important Diarylheptanoids and Their Oxa- and Fluoro Analogues by Three Different Strategies

Alexander Baranovsky, Bettina Schmitt, Daniel J. Fowler, and Bernd Schneider*

Max-Planck Institute for Chemical Ecology, Beutenberg Campus, Winzerlaer Str. 10, D-07745 Jena, Germany

Wittig reaction, aldol reaction and Wittig-Horner reaction have been used to synthesize new diarylheptanoids and analogues, which are considered intermediates of phenylphenalenone biosynthesis in plants.

Abstract

Synth. Commun. 2003, 33, 1047

New Access to Pseudo-ionones and Pseudo-iso-methyl Ionones from Geranyl Derivatives

B. Boulin,¹ B. Arreguy-San Miguel,² and B. Delmond^1,*

Laboratoire de Chimie des Substances Végétales, Institut du Pin, Université Bordeaux 1, 351 cours de la Libération, 33405 Talence Cedex, France, Unité d'Enseignement et de Recherche des Sciences Pharmaceutiques, Université Bordeaux 2, France

Pseudo-ionones 1 and pseudo-iso-methyl ionones 2, were obtained from geranyl or neryl chlorides 3, via keto-sulfides 5.

Abstract

Synth. Commun. 2003, 33, 1057

Ion Exchange Catalysis in Oxidation of Organic Compounds with KMnO₄

Ahmad Shaabani,^1,* Fatemeh Teimouri,¹ and Donald G. Lee²

Department of Chemistry, Shahid Beheshti University, P.O. Box 19396-4716, Tehran, Iran, ²Department of Chemistry, University of Regina, Regina, SK 0AS 0A2, Canada

The oxidation of organic compounds under ion exchange resin (IER) catalysis by KMnO₄ has been studied in CH₂Cl₂ under reflux conditions.