Graphical Abstracts

Abstract

Synth. Commun. 2003, 33, 175

New Synthesis of Optically Active α-Arylpropanoic Acid: The Asymmetric Hydrogenation of Atropic Acid Over Cinchona-Modified Pd/Fe₂O₃ Catalysts

H.-Zh. Ma, B. Wang,* and Q.-Zh. Shi

Department of Chemistry, Northwest University, Shaanxi Key Laboratory of Physico-Inorganic Chemistry, 710068, Xi’An, P.R. China

The first satisfactory application of the heterogeneous cinchona-modified Pd/Fe₂O₃ catalyst system in the synthesis of optically active α-arylpropanoic acid, namely, the highly enantioselective (up to 87% ee) hydrogenation of atropic acid to S-(+)-naproxen is described.

Abstract

Synth. Commun. 2003, 33, 183

An Easy and Clean Synthesis of Chiral 3,4-Diaryl-2,5-diazabicyclo[4.4.0]decanes by Reductive Intramolecular Coupling of Chiral Diimines

Peter Hesemann, Joël J. E. Moreau,* and Thierry Soto

Laboratoire de Chimie Organométallique, UMR 5076 E.N.S.C.M., 8, rue de l’Ecole Normale, 34296 Montpellier Cédex 05, France

A clean and efficient reductive intramolecular coupling of diimines prepared from (1R,2R)-cyclohexanediamine gave chiral 2,3-diarylpiperazines.

Abstract

Synth. Commun. 2003, 33, 191

Speedy and Regioselective 1,2-Reduction of Conjugated α,β-Unsaturated Aldehydes and Ketones Using NaBH₄/I₂

Jasvinder Singh,* Irvinder Kaur, Jasamrit Kaur, Aman Bhalla, and Goverdhan L. Kad

Department of Chemistry, Panjab University, Chandigarh 160 014, India

A simple and convenient regioselective 1,2-reduction of conjugated α,β-unsaturated aldehydes/ketones has been achieved using NaBH₄/I₂.

Abstract

Synth. Commun. 2003, 33, 199

Synthesis and Characterization of Homologue of Irganox 1076—Some Novel Observations

Jigar Desai,¹ A. N. Misra,² and K. B. Nair^1,*

Department of Chemistry, Faculty of Science, M.S. University of Baroda, Baroda 390 002, Gujarat, India

Gujarat Alkalies and Chemicals Limited, P.O. Petrochemical 391 346, Baroda, Gujarat, India

Homologue of Irganox 1076 is synthesized from phenol 1. Intramolecular migration and de-tert-butylation is observed in the presence of Lewis acid during Friedel–Crafts succinolyation of phenol 1.

Abstract

Synth. Commun. 2003, 33, 207

A Facile Hydration of Nitriles into Amides by Al₂O₃/MeSO₃H (AMA)

Hashem Sharghi* and Mona Hosseini Sarvari

Department of Chemistry, College of Science, Shiraz University, Shiraz 71454, I.R. Iran

A new and practical method for the conversion of nitriles to amides by employing the Al₂O₃/MeSO₃H (AMA) is described.

Abstract

Synth. Commun. 2003, 33, 213

CAN-Mediated Oxidative Free Radical Reactions in an Ionic Liquid

Gregory Bar, Fabien Bini, and Andrew F. Parsons*

Department of Chemistry, University of York, Heslington, York, UK, YO10 5DD

Cerium(IV) ammonium nitrate-mediated oxidative radical reactions are carried out in the presence of ionic liquids, including 1-butyl-3-methylimidazolium tetrafluoroborate, for the first time. The presence of the ionic liquid not only increases the rate and yield of reactions in dichloromethane but also extends the range of 1,3-dicarbonyl precursors, which can be utilized in these carbon–carbon bond-forming reactions.

Abstract

Synth. Commun. 2003, 33, 223

Redox Isomerization of Allylic Alcohols and Amides Using Grubbs’ Catalyst

E. S. Greenwood,¹ P. J. Parsons,^1,* and M. J. Young²

The Chemical Laboratories, School of Chemistry, Physics & Environmental Science, University of Sussex, Falmer, Brighton, East Sussex, BNI 9QJ UK

PR&D, Astra Zeneca, Severn Road, Hallen, Bristol, BS10 7ZE UK

Commercially available Grubbs’ catalyst was found to catalyze the redox isomerization of allylic alcohols and amides under mild conditions.

Abstract

Synth. Commun. 2003, 33, 229

N -Methylpyrrolidine-zinc Borohydride: As a New Stable and Efficient Reducing Agent in Organic Synthesis

M. Tajbakhsh,* M. M. Lakouraj,* F. Mohanazadeh, and A. Aahmadyan-nejhad

Institute of Chemistry, Mazandran University, Babolsar 47415, Iran

N-Methylpyrrolidine-zinc borohydride is easily prepared and used for reduction of a variety of organic compounds such as aldehydes, ketones, acid chlorides, and carboxylic esters. Reactions are performed in THF at room temperature and the yields are excellent.

Abstract

Synth. Commun. 2003, 33, 237

One Pot Synthesis of 3-Substituted 2 H -Naphtho[1,2-e][1,4]diazepin-2,5(1 H ,4 H  )-diones

M. Mamatha and M. Satyanarayana Reddy*

Department of Chemistry, Osmania University, Hyderabad 500 007, A.P., India

Synthesis of 3-substituted 2H-naphtho[1,2-e][1,4]diazepin-2,5(1H,4H )-diones (2) from the reaction of 2H-naphth[1,2-e][3,1]oxazin-2,4-(1H )-dione (1) with α-amino acids is reported.

Abstract

Synth. Commun. 2003, 33, 243

1,3-Dipolar Cycloaddition Reaction of C -Acetyl- N -arylnitrilimines with Selected Aliphatic Benzoylhydrazones

Abdel-Rahman S. Ferwanah

Chemistry Department, Faculty of Science, Al-Azhar University of Gaza, P.O. Box 1277, Gaza, Palestine

C-Acetyl-N-arylnitrilimines (2) react with acetaldehyde, alkanone, and cycloalkanone benzoylhydrazones (3) to give 4-benzoylamino-4,5-dihydro-1,2,4-triazoles (4–15).

Abstract

Synth. Commun. 2003, 33, 253

Novel Synthesis of N -Aroylaminated Pyridones via Reaction of Ketene Dithioacetals with Cyanoaceto- N -aroylhydrazides

Galal H. Elgemeie,^1,* Ahmed H. Elghandour,² Ali M. Elzanate,² and Ghada W. Abd Elaziz²

Chemistry Department, Faculty of Science, Helwan University, Helwan, Cairo, Egypt

Chemistry Department, Faculty of Science, Cario University, Beni-Suef Branch, Beni-Suef, Egypt

A novel synthesis of N-aroylamino-2-pyridones 6 via reaction of ketene dithioacetal 1 with cyanoaceto-N-aroylhydrazides 2 is reported and the synthetic potential of the method is demonstrated.

Abstract

Synth. Commun. 2003, 33, 259

Synthesis and Characterization of Thymidine Adducts of Arylamines

N. V. Anil Kumar and K. S. Rangappa*

Department of Studies in Chemistry, Manasa Gangotri, University of Mysore, Mysore 570 006, India

The synthesis of adducts (4) of arylamines (1) with nucleoside having pyrimidine ring system are reported.

Abstract

Synth. Commun. 2003, 33, 265

Generation of Oxyallyl Cations by Reduction of α,α′-Diiodoketones Under Sonochemical or Thermal Conditions: Improved Methodology for the [4C(4𝛑)+3C(2𝛑)] Cycloaddition Reactions

Angel M. Montaña* and Pedro M. Grima

Departamento de Química Orgánica, Universidad de Barcelona, c/ Martí i Franquès 1-1, 08028 Barcelona, Spain

New methodology to carry out [4+3] cycloaddition reactions of dienes and oxyallyl cations, which are generated in situ from α,α′-diiodoketones, by reduction with Zn/Cu couple, under ultrasound sonochemical conditions at low temperatures (from 0°C to −44°C) and for short reaction times (<15 min).

Abstract

Synth. Commun. 2003, 33, 281

Hydrazinium Monoformate: A New Hydrogen Donor. Selective Reduction of Nitrocompounds Catalyzed by Commercial Zinc Dust

Shankare Gowda, B. K. Kempe Gowda, and D. Channe Gowda*

Department of Studies in Chemistry, University of Mysore, Manasagangotri, Mysore 570 006, Karnataka, India

Nitrocompounds are selectively and rapidly reduced to their corresponding amines in the presence of other functional groups, by employing commercial zinc dust hydrazinium monoformate, a new hydrogen donor.

Abstract

Synth. Commun. 2003, 33, 291

Palladium Mediated Chemoselective Reduction of α,β-Unsaturated Cyano Esters with Potassium Formate

Basudeb Basu,* Md. Mosharef Hossain Bhuiyan, and Satadru Jha

Department of Chemistry, University of North Bengal, P.O. North Bengal University, Darjeeling 734 430, India

A number of α,β-unsaturated cyanoesters have been chemoselectively reduced with potassium formate as hydrogen donor, and palladium(II) acetate as homogeneous catalyst, in DMF without any concomitant reduction of cyano or carboxylate or halogen groups.

Abstract

Synth. Commun. 2003, 33, 297

A Simple and Convenient Procedure for the Conversion of Esters to Secondary Amides

Brindaban C. Ranu* and Pinak Dutta

Department of Organic Chemistry, Indian Association for the Cultivation of Science, Jadavpur, Calcutta 700 032, India

An improved procedure has been developed for the direct conversion of carboxylic esters to secondary amides by simple treatment with primary amines in presence of indium triiodide.

Abstract

Synth. Commun. 2003, 33, 303

Lactim Ethers in the Synthesis of 1,2-Polymethylene-4-quinazolones

Konstantin G. Nazarenko, Tatyana I. Shyrokaya, and Andrei A. Tolmachev*

Institute of Organic Chemistry, National Academy of Sciences of Ukraine, Murmanskaya 5, Kyiv-94, 02094 Ukraine

A new and convenient procedure for the preparation of 5,7,8,9,10,11-hexahydroazepino[1,2-a]quinazolin-5-ones and 1,2,3,4-tetrahydropyrrolo[1,2-a]quinazolin-5-one is described.

Abstract

Synth. Commun. 2003, 33, 311

A General Uncatalyzed Method for the Synthesis of O- Silylated Oximes

M. Ortiz-Marciales,* M. De Jesús, D. Figueroa, J. Hernández, L. Vázquez, R. Vega, E. M. Morales, and J. A. López

Department of Chemistry, University of Puerto Rico, Humacao, PR 00791, USA

A highly efficient and convenient method for the general silylation of oximes is presented.

Abstract

Synth. Commun. 2003, 33, 325

High Yield, One-Pot Synthesis of Symmetrical Diaryl- N , N -Dialkyl Carbamoylmethylphosphine Oxide (CMPO) Ligands

Paulette Guillory,¹ Ramesh N. Kapoor,¹ Keith H. Pannell,^1,* Louis Schulte,^2, Steven D. McKee,² Zhi-Yi Zhang,³ and Richard C. Bartsch³

University of Texas at El Paso, El Paso, TX 79968, USA

Los Alamos National Laboratory, Los Alamos, NM, 87545 USA

Texas Tech University, Lubbock, TX 79409, USA

A one-pot synthesis of the actinide extraction ligand 1a.

Abstract

Synth. Commun. 2003, 33, 331

Preparation of α-Methylene Ketones by Direct Methylene Transfer

J. Augusto R. Rodrigues,* Ezequias P. Siqueira-Filho, Moacir de Mancilha, and Paulo J. S. Moran

Universidade Estadual de Campinas, Instituto de Química, 13083-970 Campinas SP, Brazil

Four methods for the preparation of α-methylene ketones by I direct methylene transfer are presented. The procedures were optimized in order to obtain high yields.

Abstract

Synth. Commun. 2003, 33, 341

Synthesis of Novel Functionalized N -Tosylaldimines

James H. Wynne, Stacy E. Price, Jeffrey R. Rorer, and Wayne M. Stalick*

Department of Chemistry, George Mason University, Fairfax, VA 22030, USA

Condensation of a variety of aromatic aldehydes with p-toluenesulfonamide affords novel functionally varied aromatic N-tosylaldimines in good yields. Some of these functionalities are reported for the first time.