Graphical Abstracts

Abstract

Synth. Commun. 2005, 35, 1427

Facile Synthesis of β‐Azidocyclopropanecarboxylates by MIRC Reaction

Jiangtao Su, Guofu Qiu, Shucai Liang, and Xianming Hu

College of Pharmacy, Wuhan University, Wuhan, China

Two β‐azidocyclopropanecarboxylates are readily synthesized in the lab from β‐bromoalkyliden malonates via a Michael‐initiated ring closure (MIRC) reaction in moderate yields, which are regarded as precursors of β‐aminocyclopropanecarboxylic acids. They are important building blocks in the organic synthesis.

Abstract

Synth. Commun. 2005, 35, 1435

Novel Process for Synthesis of 1,2,4‐Triazoles: Ytterbium Triflate–Catalyzed Cyclization of Hydrazonyl Chlorides with Nitriles

Weike Su, Dianwen Yang, and Jianjun Li

College of Pharmaceutical Sciences, Zhejiang University of Technology, Hangzhou, China

A series of 1,3,5‐trisubstituted 1,2,4‐triazoles were synthesized via the intermolecular cyclization of hydrazonyl chlorides with nitriles catalyzed by ytterbium triflate [Yb(OTf)₃]. The amount of catalysis was discussed and Yb(OTf)₃ could be reused without loss of activity.

Abstract

Synth. Commun. 2005, 35, 1441

Efficient and Catalytic Conversion of Epoxides Into 1,3‐Dioxolanes with LiBF₄

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

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

Lithium tetrafluoroborate catalysis gives the efficient conversion of epoxides with acetone to the corresponding 1,3‐dioxolanes in excellent isolated yields.

Abstract

Synth. Commun. 2005, 35, 1447

Efficient Microscale Preparation of Isotopically Enriched 1‐[⁷⁹Br]Bromo‐2‐Fluoroethylene, [⁷⁹Br]BrHC˭CHF

Alessandro Baldan¹ and Augusto Tassan²

¹Dipartimento di Chimica Fisica, Università Ca' Foscari di Venezia, Venezia, Italy

²Dipartimento di Processi Chimici dell'Ingegneria, Università degli Studi di Padova, Padova, Italy

A new and convenient method was found for the synthesis of Br‐isotopically enriched BrHC˭CHF.

Abstract

Synth. Commun. 2005, 35, 1455

Preparation of 1‐Arylideneamino‐ and 1‐Alkylideneamino‐3‐Phenoxypropan‐2‐ol N‐Oxides—a New Type of Nitrones

Katarzyna Da¸bkowska,¹ Paulina Da¸browska,¹ Jacek Drabik,² Dorota Kopczuk,² Jan Plenkiewicz,¹ Joanna B. Strosznajder,² Monika Wielechowska¹

¹Faculty of Chemistry, Warsaw University of Technology, Noakowskiego, Warsaw, Poland

²Medical Research Center, Polish Academy of Sciences, Pawinskiego, Warsaw, Poland

1‐Hydroxyamino‐3‐phenoxypropan‐2‐ol reacted with aromatic or aldehydes yield the corresponding β‐hydroxynitrones in high yields.

Abstract

Synth. Commun. 2005, 35, 1461

Convenient Synthesis and Reactivity of Ethyl 8‐Amino‐6‐Methyl‐2,3‐Dihydro‐4H‐1‐Benzopyran‐2‐Carboxylate

Marko Anderluh, Gašper Marc, and Marija Sollner Dolenc

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

We report and comprehensively described synthesis and reactivity of ethyl 8‐amino‐6‐methyl‐3,4‐dihydro‐2H‐1‐benzopyran‐2‐carboxylate. This peptidomimetic building block provides a constrained template that allows for the introduction of various functionalities in a specific spatial orientation.

Abstract

Synth. Commun. 2005, 35, 1471

Synthesis of New Active o‐Nitrophenyl Carbamates

Monika Simon,¹ Carol Csunderlik,¹ Livius Cotarcaˇ,² Miron Teodor Ca˘proiu,³ Ion Neda,⁴ Maria Cristina Turoczi,¹ and Raffaella Volpicelli²

¹Politehnica University of Timişoara, Industrial Chemistry and Environmental Engineering Faculty, Timisoara, Romania

²Zambon Group SpA, Lonigo (VI), Italy

³C. D. Nenitescu Institute of Organic Chemistry, Burcharest, Romania

⁴InnChemTech GmbH, Braunschweig, Germany

A mild and efficient procedure for the reaction of bis(o‐nitrophenyl) carbonate with aliphatic amines has been developed.

Abstract

Synth. Commun. 2005, 35, 1481

Synthesis of 2‐Amino‐Octa‐4,7‐Dien‐1‐Ol (2): Key Intermediate for Mycothiazole Natural Product and Analogs

Graciela Mahler, Gloria Serra, and Eduardo Manta

Cátedra de Química Farmacéutica, Departamento de Química Orgánica, Facultad de Química, Udelar, Montevideo, Uruguay

Starting from L‐aminoacids, facile methods for the preparation 2‐aminocta‐4,7‐dien‐ol with different stereochemistry have been developed as key intermediates of mycothiazole and analogs.

Abstract

Synth. Commun. 2005, 35, 1493

A Facile Approach for New Dibenzo [b,f][1, 5] Diazocinones

Hernán Pessoa‐Mahana,¹ Karen G. Martínez Aránguiz,¹ Ramiro Araya‐Maturana¹ and C. David Pessoa‐Mahana,²

¹Departamento de Química Orgánica y Fisicoquímica, Facultad de Ciencias Químicas y Farmacéuticas, Universidad de Chile, Santiago 1, Chile

²Departamento de Farmacia, Pontificia Universidad Católica de Chile, Santiago 22, Chile

The preparation of new eight‐membered cycle dibenzo[b, f][1, 5]‐diazocine‐6‐(5H)‐one derivatives 11, 12 from nitro‐benzamide precursors 7, 8 is described.

Abstract

Synth. Commun. 2005, 35, 1501

Microwave‐Assisted Protection of Phenols as Tert‐Butyldimethylsilyl (TBDMS) Ethers under Solvent‐Free Conditions

Erick L. Bastos, Luiz F. M. L. Ciscato, and Wilhelm J. Baader

Instituto de Química, Universidade de São Paulo, São Paulo, Brazil

Facile method to protect several phenols in high yield and very short reaction times with tert‐butyldimethylsilyl chloride, using imidazole as catalyst, under solvent‐free conditions.

Abstract

Synth. Commun. 2005, 35, 1511

N‐Methyl,N‐(propyl‐3‐trimethoxysilyl) Aniline, an Intermediate for Anchoring Dyes on Siliceous Supports

María Comes, Luis Ángel Villaescusa, María Dolores Marcos, Ramón Martínez‐Máñez, Félix Sancenón, and Juan Soto

Centro de Investigación en Química Molecular Aplicada, Departamento de Química, Universidad Politécnica de València, Valencia, Spain

Abstract

Synth. Commun. 2005, 35, 1517

Dinitrogen Tetroxide–Impregnated Charcoal (N₂O₄/Charcoal): Selective Nitrosation of Amines, Amides, Ureas, and Thiols

Nasser Iranpoor, Habib Firouzabadi, and Ali Reza Pourali

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

Abstract

Synth. Commun. 2005, 35, 1527

Selective Oxidation of Benzylic Alcohols and Ethers and Oxidative Cleavage of Benzylic Tetrahydropyranyl, and Trimethylsilyl Ethers to Their Carbonyl Compounds by Dinitrogen Tetroxide–Impregnated Activated Charcoal (N₂O₄/Charcoal)

Nasser Iranpoor, Habib Firouzabadi, and Ali Reza Pourali

Department of Chemistry, Shiraz University, Shiraz, Iran

Abstract

Synth. Commun. 2005, 35, 1535

Facile Synthetic Route to (2S,3S)‐3‐Amino‐2‐hydroxy‐4‐phenylbutyric Acid and Its Derivatives, the Key Intermediates for HIV Protease Inhibitors

Lijun Lei, Xuchang He, and Donglu Bai

Shanghai Institute of Materia Medica, Shanghai Institutes for Biological Sciences, Chinese Academy of Sciences, Shanghai, China

Using N‐phthaloyl protected L‐phenylalanine as the starting material, a facile route to (4S, 5S)‐4‐benzyl‐5‐hydroxymethyl oxazolidin‐2‐one is presented.

Abstract

Synth. Commun. 2005, 35, 1541

KBrO₃/ZrClO₂·8H₂O: An Efficient Reagent System for the Oxidation of Alcohols

Farhad Shirini,¹ Mohammad Ali Zolfigol,² and Esmail Mollarazi¹

¹Department of Chemistry, Guilan University, Rasht, 41335, Iran

²Department of Chemistry, Bu‐Ali Sina University, Hamadan 65174, Iran

KBrO₃ in the presence of ZrOCl₂·8H₂O can be used as an effective oxidizing agent for the conversion of alcohols to their corresponding carbonyl compounds. All reactions were performed under mild and completely heterogeneous conditions in good to high yields.

Abstract

Synth. Commun. 2005, 35, 1547

Synthesis and Application of 2,6‐Dicarboxy Pyridinium Fluorochromate as a New Solid‐Phase Oxidant

M. Tajbakhsh, R. Hosseinzadeh, and M. Sadatshahabi

Department of Chemistry, Mazandaran University, Babolsar, Iran

2,6‐Dicarboxypyridinium fluorochromate was easily prepared and found to be an efficient oxidant for organic substrate under solvent‐free conditions.

Abstract

Synth. Commun. 2005, 35, 1555

In Situ Alcohol Oxidation‐Protection Reactions

A. R. Kiasat, F. Kazemi, and K. Nourbakhsh

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

The one‐pot conversion of primary and secondary alcohols into phenylhydrazones and 2,4‐dintrophenylhydrazones is reported using chromium trioxide supported on silica gel and phenylhydrazines or 2,4‐dintrophenylhydrazines under solvent‐free conditions.

Abstract

Synth. Commun. 2005, 35, 1559

Unexpected Dehydrogenation Products in the Furan Series arising from Ruthenium‐Catalyzed 4‐Oxo‐1,6‐enyne Metathesis

Laurent Evanno, Bastien Nay, and Bernard Bodo

Laboratoire de Chimie et Biochimie des Substances Naturelles, UMR 5154 CNRS, Muséum National d'Histoire Naturelle, Paris, France