Graphical Abstracts

Abstract

Synth. Commun. 2003, 33, 3089

Synthesis of β-Amino Acids: 2-(1H-Benzotriazol-1-YL)-1,1,3,3-tetramethyluronium Tetrafluoroborate (TBTU) for Activation of Fmoc-/Boc-/ Z -α-Amino Acids

Basanagoud S. Patil, Ganga-Ramu Vasanthakumar, and V. V. Suresh Babu*

Department of Studies in Chemistry, Central College Campus, Bangalore University, Dr. B. R. Ambedkar Veedhi, Bangalore, India

A new and efficient method for the homologation of Fmoc-/Boc-Z protected α-amino acids to its β-homomers by the Arndt–Eistert method using TBTU as a coupling agent is described.

Abstract

Synth. Commun. 2003, 33, 3097

A Facile Synthesis of 1,4-DiacylBenzenes

Harindran Suhana and Panyencheri C. Srinivasan*

Department of Organic Chemistry, University of Madras, Guindy Campus, Chennai, Tamil Nadu, India

An efficient method for the synthesis of 1,4-diacylbenzenes has been developed employing bis-tetrabutylammonium dichromate as an oxidant. By this methodology, a series of aldeydes and ketones have been synthesized under mild reaction conditions in moderate yields.

Abstract

Synth. Commun. 2003, 33, 3103

Regioselective Reaction of Epoxides with Disulfides Using Zn/AlCl₃ System: A Simple Synthesis of β-Hydroxy Sulfides

B. Movassagh,^1,* S. Sobhani,² F. Kheirdoush,² and Z. Fadaei³

¹Department of Chemistry, K. N. Toosi University of Technology, Tehran, Iran ²Department of Chemistry, Razi University, Kermanshah, Iran; ³Department of Chemistry, Jahad Daneshgahi, Kermanshah, Iran

Epoxides are regioselectively cleaved by zinc thiolate intermediate to afford high yields of the corresponding β-hydroxy sulfides.

Abstract

Synth. Commun. 2003, 33, 3109

An Efficient and Novel Method for the Synthesis of β-Aroylpropionic Acids Under Solvent-Free Conditions

K. Mogilaiah,* N. Vasudeva Reddy, and G. Randheer Reddy

Department of Chemistry, Kakatiya University, Warangal, India

An efficient and clean procedure for the preparation of β-aroylpropionic acids under solvent-free conditions at room temperature is reported.

Abstract

Synth. Commun. 2003, 33, 3115

Microwave-Assisted Rapid Synthesis of Neurotransmitter Release Enhancer Linopiridine and Its New Analogues

J. S. Yadav* and B. V. S. Reddy

Division of Organic Chemistry, Indian Institute of Chemical Technology, Hyderabad, India

A neurotransmitter release enhancer linopiridine and its new analogues have been synthesized rapidly in yields from the 1:2 coupling of oxiindole with 4-picolyl chloride hydrochloride on the surface of basic alumina doped with 37% KF under microwave irradiation in solvent-free conditions.

Abstract

Synth. Commun. 2003, 33, 3123

One Pot Synthesis of Aryldiazepinothiophenones

Minothora Pozarentzi, Julia Stephanidou-Stephanatou,* and Constantinos A. Tsoleridis

Department of Chemistry, Laboratory of Organic Chemistry, University of Thessaloniki, Thessaloniki, Macedonia, Greece

The aryldiazepine derivatives 2 and 3 were prepared in one-pot synthesis from the reaction of o-phenylenediamines with an excess of acetone in the presence of 2-mercaptopropionic acid.

Abstract

Synth. Commun. 2003, 33, 3131

An Efficient Friedlander Condensation Using Sodium Fluoride as Catalyst in the Solid State

K. Mogilaiah* and Ch. Srinivas Reddy

Department of Chemistry, Kakatiya University, Warangal, India

Sodium fluoride catalyzed Friedlander condensation of 2-aminonicotinaldehyde with carbonyl compounds containing α-methylene group has been achieved in the solid state to give 1,8-naphthyridine derivatives in high yields.

Abstract

Synth. Commun. 2003, 33, 3135

Synthesis and Characterization of Some New Cycloaddition Products of Bifunctional Acetylenic Ketone

R. K. Tiwari* and A. K. Saxena

Defence Materials and Stores Research and Development Establishment, Kanpur, India

Bot 2:1 and 4:1 cycloaddition products were obtained by the reaction of terephaloylacetylene with diennes, which some times rearrange too.

Abstract

Synth. Commun. 2003, 33, 3147

Solid-Phase Oxidation of alcohols and Benzyl Halides to Carbonyls using Bromate Exchange Resin

Atul Pd. Sikdar, Ajoy B. Chetri, Gakul Baishya, and Pranab J. Das*

Department of Chemistry, Gauhati University, Guwahati, India

Bromate exchange resin prepared by a simple elution technique and used for the biphasic oxidation of alcohols and benzyl halides to corresponding carbonyl compounds.

Abstract

Synth. Commun. 2003, 33, 3153

Highly Regioselective Conversion of Epoxides to β-Hydroxy Nitriles with Cyanide Exchange Resin

B. Tamami,* N. Iranpoor,* and R. Rezaei

Chemistry Department, College of Sciences, Shiraz University, Shiraz, Iran

A simple, efficient, and regioselective method for direct conversion of epoxides into β-hydroxy nitriles, in the absence of catalyst, using Amberlite IRA-400 supported cyanide is described.

Abstract

Synth. Commun. 2003, 33, 3159

Synthesis of New Macrocycles with 2,2′-Bipyridyl and Polyamine Functions

B. K. Kanungo,* Minati Baral, S. Bhattacharya, and Y. Sahoo

Department of Chemistry, Sant Longowal Institute of Engineering and Technology, Longowal, Punjab, India

A series of macrocycles with 2,2′-bipyridyl sub-units and two different complexing sites have been synthesized from 1,10-phenanthrolene in three steps and characterized on the basis of elemental anlysis, NMR, electronic, and infrared spectral data.

Abstract

Synth. Commun. 2003, 33, 3165

Alkylation of Dimethyl 1,3-Acetonedicarboxylate

Adrián Covarrubias-Zúñiga,^1,* Laura San Germán-Sanchez,¹ and José G. Avila-Zárraga²

¹Instituto de Química, and ²Facultad de Química, Universidad Nacional Autónoma de México, Ciudad Universitaria, Coyoacán, México

A reliable, reproducible, general, and detailed procedure for the alkylation of dimethyl 1,3-acetonedicarboxylate II is described.

Abstract

Synth. Commun. 2003, 33, 3173

A Total Synthesis of the Antibiotic DB-2073

Adrián Covarrubias-Zúñiga,^1,* José G. Avila-Zárraga,² and David Arias Salas¹

¹Instituto de Química, and ²Facultad de Química, Universidad Nacional Autónoma de México, Ciudad Universitaria, Coyoacán, México

A convergent synthesis of the Antibiotic DB-2073 I has been achieved.

Abstract

Synth. Commun. 2003, 33, 3183

Synthesis of a First Estradiol-Adenosine Hybrid Compound

Donald Poirier,* Roch P. Boivin, Marie Bérubé, and Sheng-Xiang Lin

Medicinal Chemistry Division, Oncology and Molecular Endocrinology Research Center and University Laval, Centre Hospitalier Universitaire de Québec (CHUQ), Pavillon CHUL, Québec, Canada

Chemical synthesis and IR, NMR, and MS characterization of a first substrate-cofactor hybrid compound that open the door to a new family of type 1 17β-HSD inhibitors.

Abstract

Synth. Commun. 2003, 33, 3193

A Convenient “One-Pot” Reaction for Selective Monoalkylation of N , N ′ -Disubstituted Ethylenediamines

Alejandra Salerno, María Amalia Figueroa, and Isabel A. Perillo*

Departamento de Química Orgánica, Facultad de Farmacia y Bioquímica, Universidad de Buenos Aires, Junín, Buenos Aires, Argentina

A study on the scope of the method to obtain N,N,N ′-trisubstituted ethylenediamines III by monoalkylation of N,N ′-disubstituted ethylenediamines I through a “one-pot” reaction is presented.

Abstract

Synth. Commun. 2003, 33, 3205

An Efficient Synthesis of 3,4-bis(Tri-n-butylstannyl)furan

Simon P. H. Mee, Victor Lee, and Jack E. Baldwin*

The Dyson Perrins Laboratory, Oxford University, Oxford, United Kingdom

An efficient synthesis of 3,4-bis(tri-n-butylstannyl)furan is achieved by palladium-catalyzed addition of hexa-n-butylditin to 2-butyne-1,4-diol, followed by oxidative cyclization and dehydration.

Abstract

Synth. Commun. 2003, 33, 3211

Efficient Hydroxyl Inversion in Propionates via Cesium Carboxylates

David O. Arbelo, Leslie Castro-Rosario, and José A. Prieto*

Department of Chemistry, University of Puerto Rico, Río Piedras Campus, San Juan, Puerto Rico, USA

A versatile method for hydroxyl inversion, based on cesium carboxylates, has been developed for polypropionate precursors and models. Some diastereomeric 3,4-epoxy alcohols that were not previously available by standard iodocyclization techniques, were prepared.

Abstract

Synth. Commun. 2003, 33, 3225

Improved Selective Reduction of 3-Formylchromones Using Basic Alumina and 2-Propanol

Ramiro Araya-Maturana,^1,* Jorge Heredia-Moya,¹ Hernán Pessoa-Mahana,¹ and Boris Weiss-López ²

¹Department of Organic and Physical Chemistry, Faculty of Chemical and Pharmaceutical Sciences, ²Department of Chemistry, Faculty of Sciences, University of Chile, Santiago, Chile

Treatment of formylchromones 1, dissolved in 2-propanol with basic alumina at 75°C, selectively reduces the formyl group with good yields without any activation process of the alumina.

Abstract

Synth. Commun. 2003, 33, 3233

Straightforward Preparation of (2E,4Z )-2,4-Heptadien-1-ol and (2E,4Z )-2,4-Heptadienal

Richard J. Petroski*

USDA, REE, Agricultural Research Service, National Center for Agricultural Utilization Research, Crop Bioprotection Research Unit, Peoria, Illinois, USA

Abstract

Synth. Commun. 2003, 33, 3243

Oxidation of Monotetrahydropyranylated Short-Chain Symmetrical Diols

Richard J. Petroski*

USDA, REE, Agricultural Research Service, National Center for Agricultural Utilization Research, Crop Bioprotection Research Unit, Peoria, Illinois, USA

The free hydroxyl functions of monotetrahydropyranylated three- to five-carbon symmetrical primary diols are oxidized to aldehydes, without cleavage of the protective group, by using pyridinium dichromate in CH₂Cl₂ and anhydrous MgSO₄ as a water scavenger. The oxidation procedure is improved for these specific compounds since over oxidation to carboxylic acids and formation of dimeric esters are suppressed.

Abstract

Synth. Commun. 2003, 33, 3251

Preparation of Monotetrahydropyranylated Short-Chain Symmetrical Diols

Richard J. Petroski*

USDA, REE, Agricultural Research Service, National Center for Agricultural Utilization Research, Crop Bioprotection Research Unit, Peoria, Illinois, USA

The preparation of 4-(tetrahydro-pyran-2-yloxy)-butan-1-ol from 1,4-butanediol and 5-(tetrahydro-pyran-2-yloxy)-pentan-1-ol from 1,5-pentanediol was accomplished using a two-phase system composed of a: CH₂Cl₂, 3,4-dihydro-2H-pyran (DHP), and aqueous 0.1 N HCl. Preparation of 3-(tetrahydro-pyran-2-yloxy)-propan-1-ol was accomplished using a water-free biphasic mixture composed of b: 1,3-propanediol, catalytic pyridinium p-toluenesulfonate, DHP, and 25% ether in hexane.

Abstract

Synth. Commun. 2003, 33, 3261

Synthesis of 5- and 6-Acyl-1-cyano- and -1-ethoxycarbonyl Cycloalkenes

Houda Kraïem, Taoufik Turki, and Hassen Amri*

Laboratoire de Chimie Organique et Organométallique Faculté des Sciences, Campus Universitaire, Tunis, Tunisia