Graphical Abstracts

Abstract

Synth. Commun. 2003, 33, 1245

Synthesis of Dihydro- and Tetrahydro-1,2,4,5-Tetrazines from the Reaction of Nitrilimines with 1-Substituted-1-Methylhydrazine

Abdel-Rahman S. Ferwanah,^1,* Adel M. Awadallah,¹ Emtithal A. El-Sawi,² and Hany M. Dalloul²

¹Chemistry Department, Faculty of Science, Islamic University of Gaza, P.O. Box-1277, Gaza, Palestine ²Chemistry Department, University College for Women, Ain Shams University, Heliopolis, Cairo, Egypt

Tetrahydro- (10,11) and dihydro-1,2,4,5-tetrazines (12) were prepared from the reaction of nitrilimines with 1-substituted-1-methylhydrazines (3–6).

Abstract

Synth. Commun. 2003, 33, 1255

Solvent Free Ion Exchange Catalysis in the Oxidation of Organic Compounds with Sodium Bromate

Ahmad Shaabani^1,* and Donald G. Lee²

¹Chemistry Department, Shahid Beheshti University, P.O. Box 19396-4716, Tehran, Iran; ²Department of Chemistry, University of Regina, Regina SK S4 S0A2, Canada

The oxidation of organic compounds under solvent free ion exchange resin (IER) catalysis by sodium bromate has been studied at room temperature.

Abstract

Synth. Commun. 2003, 33, 1261

Synthesis of ( E  ) α,2,4-Trinitrostilbenes from ( E  ) 2,4-Dinitrostilbenes

S. Saravanan and P. C. Srinivasan*

Department of Organic Chemistry, University of Madras, Guindy Campus, Chennai 600 025, India

A convenient synthesis of (E ) α,2,4-trinitrosstilbenes 2a–d from (E ) 2,4-dinitrostilbenes la–e by direct nitration is reported. Isomerization of the trans geometry of the reactant stilbenes to cis in the products was found. The structures of stilbenes 2a–c were confirmed by XRD.

Abstract

Synth. Commun. 2003, 33, 1267

An Efficient Synthesis of 2-Alkylthio-5-phenylmethylidene-4 H -imidazolin-4-ones

Ming-Wu Ding,* Yong Sun, and Zhao-Jie Liu

Institute of Organic Synthesis, Central China Normal University, Wuhan, 430076, P.R. China

Abstract

Synth. Commun. 2003, 33, 1275

Studies on the Synthesis of Novel Chiral Naphthylene Bisoxazoline Ligands

Zhan-Yue Wang, Da-Ming Du,* Di Wu, and Wen-Ting Hua

Key Laboratory of Bioorganic Chemistry and Molecular Engineering of Ministry of Education, College of Chemistry and Molecular Engineering, Peking University, Beijing 100871, P.R. China

The synthesis of chiral C₂-symmetric substituted bisoxazoline ligands containing naphthalene group were investigated. Ethyl 2,3-naphthylene-dicarboxylate reacted with amino alcohols and the resulting amides were treated with SOCl₂ and then reacted with Et₃N in toluene to afford the desired bisoxazolines.

Abstract

Synth. Commun. 2003, 33, 1285

Studies on the Preparation of 4-Ethoxyalkyliden and 4-Aminoalkyliden–5(4 H )-Oxazolones

Marta R. P. Norton Matos, Pedro M. P. Gois, Maria L. E. N. Mata, Eurico J. Cabrita, and Carlos A. M. Afonso*

REQUIMTE/CQFB, Departamento de Química, Faculdade de Ciências e Tecnologia, Universidade Nova de Lisboa, 2829-516 Caparica, Portugal

Optimized conditions for the preparation of 4-ethoxyalkyliden-5(4H)-oxazolones 1 were developed. A considerable steric hindrance was observed on the preparation of 4-aminoalkyliden-5(4H)-oxazolones 2 by nucleophilic substitution of the ethoxy group by amines.

Abstract

Synth. Commun. 2003, 33, 1301

Synthesis of 2-(Polyhydroxy)Alkyl- and 2-(6-Adenosinyl)BenzisoselenAzol-3(2 H )-Ones

Mariusz Osajda and Jacek Młochowski*

Institute of Organic Chemistry, Biochemistry and Biotechnology, Wrocław University of Technology, 50-370 Wrocław, Poland

Synthesis of title compounds as potential virucides based on acylation–selenylation of primary amino groups in aminopolyols or adenosine with 2-(chloroseleno)benzoyl chloride.

Abstract

Synth. Commun. 2003, 33, 1309

Synthesis of Antibiotic Stilbenes by Reductive Metalation of 3,4,5-Trimethoxybenzaldehyde Dimethyl Acetal

Ugo Azzena,* Maria Vittoria Idini, and Luciano Pilo

Dipartimento di Chimica e Facoltà di Farmacia, Università di Sassari, via Vienna 2, 1-07100 Sassari, Italy

Abstract

Synth. Commun. 2003, 33, 1319

Iodination of Aromatic Compounds with Iodine and n -ButylTriphenylphosphonium Peroxodisulfate

H. Tajik,^1,* A. A. Esmaeili,² I. Mohammadpoor-Baltork,³ A. Ershadi,² and H. Tajmehri¹

¹Department of Chemistry, College of Science, Guilan University, Rasht-Iran ²Department of Chemistry, College of Science, Beerjand University, Beirjand-Iran ³Department of Chemistry, College of Science, Isfahan University, Isfahan, Iran

Iodine and n-butyltriphenylphosphonium peroxodisulfate can be successfully used for the iodination of some aromatic compounds in acetonitrile as solvent. The yields obtained are good to excellent.

Abstract

Synth. Commun. 2003, 33, 1325

Selective Oxidation of Benzylic Substrates to Their Corresponding Carbonyl Compounds with 3,6- Bis (Triphenylphosphonium)cyclohexene Peroxodisulfate

Rashid Badri* and Mousa Soleymani

Department of Chemistry, Chamran University, Ahvaz, Iran

The oxidation ability of the title compound as an effiicient selective oxidant for benzylic subsrates is reported.

Abstract

Synth. Commun. 2003, 33, 1333

An Efficient Co(II) Catalyzed Auto Oxidation of 1,4-Dihydropyridines

Subhash P. Chavan,* Rajendra K. Kharul, Uttam R. Kalkote, and I. Shivakumar

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

An efficient Co(II) catalyzed auto oxidation of 1,4-dihydropyridines to pyridines in good to excellent yields is described.

Abstract

Synth. Commun. 2003, 33, 1341

New Phosphono Substituted-3- and 5-Membered Rings Starting from 3(2-ThienyL)Acrylonitriles and α-Phosphoryl Carbanions

Wafaa M. Abdou,^1,* Mounir A. I. Salem,² and Reham F. Barghash¹

¹National Research Centre, Dokki, Cairo, Egypt ²Department of Chemistry, Faculty of Science, Ain-Shams University, Cairo, Egypt

A series of the title compounds were synthesized using the α-phosphoryl carbanions 2a–c on 3(2-thienyl)acrylonitriles 1a,b in the presence of different bases.

Abstract

Synth. Commun. 2003, 33, 1359

Efficient Tetrahydropyranylation of Phenols and Alcohols Catalyzed by Supported MO and W Keggin Heteropolyacids

G. P. Romanelli,^1,2 P. G. Vázquez,² L. R. Pizzio,² C. V. Cáceres,² M. N. Blanco,² and J. C. Autino^1,*

¹LADECOR, Laboratorio de Estudio de Compuestos Orgánicos, Departamento de Química, Facultad de Ciencias Exactas, Universidad Nacional de La Plata, La Plata Calles 47 y 115, B1900AJL La Plata, Argentina ²CINDECA, Centro de Investigación en Procesos Catalíticos, Departamento de Química, Facultad de Ciencias Exactas, Universidad Nacional de La Plata–CONICET Calle 47 Nro 257, B1900AJK La Plata, Argentina

Tetrahydropyranylation of phenols and alchohols catalyzed by silica supported Mo and W Keggin heteropolyacids (PMo₁₂O₄₀H₃ and PW₁₂O₄₀H₃).

Abstract

Synth. Commun. 2003, 33, 1367

Catalytic Friedel-Crafts Acylation of Alkoxy Benzenes by Ferric Hydrogensulfate

Peyman Salehi,^1,* Mohammad Mahdi Khodaei,² Mohammad Ali Zolfigol,³ and Shahpour Zeinoldini²

¹Department of Phytochemistry, Medicinal Plants Research Institute, Shahid Beheshti University, Evin, Tehran, Iran ²Department of Chemistry, Faculty of Science, Razi University, Kermanshah, Iran ³Department of Chemistry, Faculty of Science, Bu-Ali Sina University, Hamadan, Iran

Friedel-Crafts acylation of alkoxy benzenes is achieved efficiently by reaction with aliphatic acid anhydrides in the presence of catalytic amounts of ferric hydrogensulfate, Fe(HSO₄)₃, in nitromethane.

Abstract

Synth. Commun. 2003, 33, 1375

A Synthesis of Racemic Thalidomide

Meng-Yang Chang,¹ Shui-Tein Chen,¹ and Nein-Chen Chang^2,*

¹Institute of Biological Chemistry, Academia Sinica, Nankang, Taipei, Taiwan ²Department of Chemistry, National Sun Yat-Sen University, Kaohsiung 804, Taiwan

A synthesis of racemic thalidomide is described using formal [3 + 3] cycloaddition strategy as the key step. The total yield of thalidomide was 30% in three steps from ester 2.

Abstract

Synth. Commun. 2003, 33, 1383

The Use of DMAP as Catalyst in the Baylis-Hillman Reaction Between Methyl Acrylate and Aromatic Aldehydes

Rodrigo Octavio, M. A. de Souza, and Mário Luiz A. A. Vasconcellos*

Núcleo de Pesquisas de Produtos Naturais–Universidade Federal do Rio de Janeiro, Centro de Ciências da Saúde, Ilha do Fundão, RJ Brazil

Abstract

Synth. Commun. 2003, 33, 1391

Syntheses of cis - and trans -7-Chloro-7,8,9,10-Tetrahydrobenzo[ a ]Pyren-8-Ol: A Remarkable Solvent Effect on Epoxide Hydrochlorination Diastereoselectivity

Mathew P. D. Mahindaratne,^# Hesham T. Y. Fahmy,^‡ Jesus A. Garcia, and George R. Negrete*

Department of Chemistry, University of Texas at San Antonio, San Antonio, TX 78249-0698

A dramatic solvent effect on the hydrochlorination of an aryl epoxide allows the highly selective preparation of either the cis or trans chlorohydrin.

Abstract

Synth. Commun. 2003, 33, 1399

Studies on Bromination of Active Methylene by a Mixture of Hydrobromic Acid and Hydrogen Peroxide (or TBHP)

Vasudha H. TiIlu, Popat D. Shinde, Ashutosh V. Bedekar, and Radhika D. Wakharkar*

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

Studies on bromination of active methylme with a mixture of hydrogen peroxide or tert-butylhydroperoxide (TBHP) and hydrobromic acid are discussed. Substituted acetophenones, benzocyclic ketones provide α-bromo-keto compounds in high yields under this reaction condition.

Abstract

Synth. Commun. 2003, 33, 1405

Microwave Assisted Aromatic Nucleophilic Substitution Reaction Under Solventless Condition

Geeta L. Rebeiro* and Bhushan M. Khadilkar^‡

Organic Chemistry Research Laboratory, Applied Chemistry Division, University Institute of Chemical Technology, Matunga, Mumbai 400 019, India

We report here microwave assisted aromatic nucleophilic substitution reaction of 1-chloro-4-nitrobenzene with different phenoxides.

Abstract

Synth. Commun. 2003, 33, 1411

Synthesis of N -Methyl Secondary Amines

Hephzibah J. Kumpaty,¹ John S. Williamson,² and Sukanta Bhattacharyya^3,*

¹Department of Chemistry, University of Wisconsin–Whitewater, WI-53190, USA ²Department of Medicinal Chemistry, School of Pharmacy, The University of Mississippi, Mississippi, MS 38977, USA ³Argonaut Technologies, Foster City, CA 94404, USA

A rapid, high-yielding method for the preparation of N-methyl secondary amines is described.

Abstract

Synth. Commun. 2003, 33, 1417

First Total Synthsis of (±)Hedaol B

Ying Li,* Biao Lu, Chunhong Li, and Yulin Li

National Laboratory of Applied Organic Chemistry and Institute of Organic Chemistry, Lanzhou University, Lanzhou 730000, P.R. China

Hedaol B, a new bisnorditerpene isolated from the Japanese brown alga sargassum. sp., was first synthesized starting from geranyl acetone, alkylation of silyl cyanide as the step.