Graphical Abstracts

Abstract

Graphical Abstract Section

Abstract

Synth. Commun. 2008, 38, 656

STABLE OXYPYRIDINIUM TRIFLATE (OPT) SALTS FOR THE SYNTHESIS OF HALOBENZYL ETHERS

Philip A. Albiniak, Shawn M. Amisial, Gregory B. Dudley, Joseph P. Hernandez, Sarah E. House, Margaret E. Matthews, Ernest O. Nwoye, Maureen K. Reilly, and Sami F. Tlais

Department of Chemistry and Biochemistry, Florida State University, Tallahassee Florida, USA

Abstract

Synth. Commun. 2008, 38, 666

CATALYST‐FREE ONE‐POT SYNTHESIS OF 2,4,6‐TRIARYL‐1,4‐DIHYDROPYRIDINES IN IONIC LIQUID AND THEIR CATALYZED ACTIVITY ON TWO SIMPLE DIELS–ALDER REACTIONS

Hui Wu,^1,2 Yu Wan^1,2, L. L. Lu,³ Yang Shen,¹ L. Ye¹, and F. R. Zhang¹

¹School of Chemistry and Chemical Engineering, Xuzhou Normal University, Xuzhou, Jiangsu, China

²Key Laboratory of Biotechnology on Medical Plants of Jiangsu Province, Xuzhou, Jiangsu, China

³Department of Chemical and Textile Engineering, Jiangyin Polytechnic College, Jiangyin, Jiangsu, China

A series of 2,4,6-triaryl-1,4-dihydropyridines bearing hydroxyl were synthesized greenly by the cascade aldol/Michael/addition reaction of aromatic aldehyde, acetophenone and NH₄OAc (1:2:excessive) in ionic liquid [BmIm][BF₄] without any catalyst. The results of their catalyzed activity on two simple Diels–Alder reactions indicated that this kind of compound containing a poly aryl ring can be used as an effective catalyst on the Diels–Alder reaction. This method, because of its environmental friendliness, simplicity, mild conditions, effectiveness, and lower costs, is suitable for the synthesis of arrays of compounds.

Abstract

Synth. Commun. 2008, 38, 674

SYNTHESIS OF 3‐SUBSTITUTED‐1‐METHYL‐1H‐THIENO[2,3‐ c ]PYRAZOLES

Patrick Toto,¹ Jacques Chenault,¹ Ahmed El Hakmaoui,² Mohamed Akssira,² and Gerald Guillaumet¹

¹Analytic and Organic Chemistry Institute, University of Orleans, UMR CNRS, Orleans Cedex, France

²Analytic and Bioorganic Chemistry Laboratory, Faculty of Sciences and Technology, University Hassan II Mohammedia, Mohammedia, Morocco

Abstract

Synth. Commun. 2008, 38, 684

ASYMMETRIC REDUCTION OF PROCHIRAL KETONES WITH N‐SULFONYLATED AMINO ALCOHOLS AS CATALYSTS

Zhongqiang Zhou and Yajing Guo

Key Laboratory of Catalysis and Materials Science of Hubei Province, College of Chemistry and Materials Science, South‐Central University for Nationalities, Wuhan, China

Novel N‐sulfonylated amino alcohols were synthesized from L‐amino acids and (+)‐camphor, and their application to asymmetric reduction of prochiral ketones is described.

Abstract

Synth. Commun. 2008, 38, 697

NEW SYNTHESIS OF 2,2‐BIS(HYDROXYMETHYL)METHYLENECYCLOPROPANE, A KEY INTERMEDIATE FOR ANTIVIRAL CYCLOPROPAVIR

Gopinath Tiruchinapally and Jiri Zemlicka

Developmental Therapeutics Program, Barbara Ann Karmanos Cancer Institute, Wayne State University School of Medicine, Detroit, Michigan, USA

Abstract

Synth. Commun. 2008, 38, 703

C‐VINYLATION OF 1,8‐DIHYDROXYANTHRAQUINONE PROMOTED BY TRIPHENYLPHOSPHINE

Issa Yavari,^1,2 Ali R. Alborzi,² Bita Mohtat,² and Farahnaz Nourmohammadian³

¹Chemistry Department, Tarbiat Modares University, Tehran, Iran

²Chemistry Department, Science and Research Campus, Islamic Azad University, Tehran, Iran

³Department of Colorant Manufacture, Iran Color Research Center, Tehran, Iran

Abstract

Synth. Commun. 2008, 38, 713

PREPARATION OF 4,5‐DIHYDRONAPHTH[2,1‐c]ISOXAZOLES FROM DILITHIATED 2‐TETRALONE OXIME AND SELECT ESTERS

Emily Choi, John D. Knight, Maria D. Malatanos, J. Matthew Rhett, Matthew J. Walters, S. Patrick Dunn, and Charles F. Beam

Department of Chemistry and Biochemistry, College of Charleston, Charleston, South Carolina, USA

Abstract

Synth. Commun. 2008, 38, 723

COPPER‐CATALYZED COUPLING REACTION OF 2‐THIOXO‐4‐QUINAZOLINONE AND THIENO[3,2‐ D ]PYRIMIDIN‐4‐ONE METHANE SULPHONAMIDE WITH ARYL IODIDES: PREPARATION OF POTENTIAL COX‐2 SELECTIVE INHIBITORS

Antonio Perdicaro, Giuseppe Granata, Agostino Marrazzo, and Andrea Santagati

Department of Pharmaceutical Science, University of Catania, Catania, Italy

Abstract

Synth. Commun. 2008, 38, 738

PRACTICAL METHYLATION PROCEDURE FOR (1H)‐1,2,4‐TRIAZOLE

John L. Belletire,¹ Robert A. Bills,² and Scott A. Shackelford²

¹ERC Incorporated, Air Force Research Laboratory, Edwards Air Force Base, California, USA

²Air Force Research Laboratory, Space and Missile Propulsion Directorate, Propellants Branch, Edwards Air Force Base, California, USA

Abstract

Synth. Commun. 2008, 38, 746

DIMETHYL SULFOXIDE PIVALOYL CHLORIDE: A NEW REAGENT FOR OXIDATION OF ALCOHOLS TO CARBONYLS

Abhishek Dubey, Subba Rao V. Kandula and Pradeep Kumar

Division of Organic Chemistry, National Chemical Laboratory, Pune, India

Abstract

Synth. Commun. 2008, 38, 754

ALUMINIUM CHLORIDE–CATALYZED CLAISEN REARRANGEMENT: SYNTHESIS OF POLYHETEROCYCLES CONTAINING OXYGEN, NITROGEN, AND SULFUR

K. C. Majumdar, R. Islam, and S. Alam

Department of Chemistry, University of Kalyani, Kalyani, India

Abstract

Synth. Commun. 2008, 38, 767

SYNTHESIS OF AZIDO HETEROCYCLES

Raja Duddu,¹ Paritosh R. Dave,¹ Reddy Damavarapu,² Rao Surapaneni,² Richard Gilardi,³ and Damon Parrish³

¹SAIC at ARDEC, Picatinny, New Jersey, USA

²U.S. Army ARDEC, Picatinny, New Jersey, USA

³Laboratory for the Structure of Matter, Naval Research Laboratory, Washington, D.C., USA

Syntheses azido derivatives of hexaazaisowurtzitane, triazine, and tetrazine heterocyclic compounds are described.

Abstract

Synth. Commun. 2008, 38, 775

SYNTHESIS AND CHARACTERIZATION OF DIBENZODIOXAZASILADECINES

M. S. Singh and Pratibha Singh

Faculty of Science, Department of Chemistry, Banaras Hindu University, Varanasi, India

The reaction of N‐(2‐hydroxymethylphenyl)salicylidene‐imine with sodium hydride in dry toluene at −4°C produces 1,9‐remote dianion. The cyclization of this dianion with diorganodichlorosilanes affords dibenzodioxazasiladecines in good yields. The products were characterized by satisfactory elemental analyses and spectral (IR, ¹H, ¹³C, and ²⁹Si NMR and mass) studies.

Abstract

Synth. Commun. 2008, 38, 784

IMPROVED SOLVENT‐FREE DAKIN OXIDATION PROTOCOL

Emerson Teixeira da Silva,^1,2 Celso Amorim Câmara,³ O. A. C. Antunes,^1,2 Eliezer J. Barreiro,⁴ and Carlos A. M. Fraga⁴

¹Chemistry Institute, Federal University of Rio de Janeiro, Cidade Universitária, Rio de Janeiro, Brazil

²Nortec Química, Duque de Caxias, Brazil

³Chemistry Department, Rural Federal University of Pernambuco, Recife, Brazil

⁴Laboratório de Avaliação e Síntese de Substâncias Bioativas, Federal University of Rio de Janeiro, Faculty of Pharmacy, Rio de Janeiro, Brazil

Solvent‐free Dakin reaction with mCPBA was accomplished with various aromatic aldehydes, resulting in an easy and improved methodology for the preparation of corresponding phenols. 3,4‐Methylenedioxyphenol, 3,4‐dimethoxyphenol, 4‐methoxyphenol, 4‐chlorophenol, and others were obtained in high from the corresponding aromatic aldehydes in a few minutes by using this new efficient methodology.

Abstract

Synth. Commun. 2008, 38, 789

IN SITU GENERATION OF n‐BUTANETHIOL AND ITS REACTION WITH ELECTRON‐DEFICIENT OLEFINES

Rogério A. Gariani,¹ Alcindo A. Dos Santos,² and João V. Comasseto³

¹Instituto de Química, Universidade de São Paulo, São Paulo, Brazil

²Departamento de Química, Universidade Federal de São Carlos, São Carlos, Brazil

³Instituto de Química, Universidade de São Paulo, São Paulo, Brazil

Abstract

Synth. Commun. 2008, 38, 796

PRACTICAL ONE‐POT PROCEDURE FOR THE SYNTHESIS OF 1,2,3,4‐TETRAHYDROQUINOLINES BY THE IMINO–DIELS–ALDER REACTION

Christoph M. Dehnhardt, Yomery Espinal, and Aranapkam M. Venkatesan

Chemical and Screening Sciences, Wyeth Research, Pearl River, New York, USA

A novel‐one‐pot procedure for the synthesis of tetrahydroquinolines via the imino–Diels–Alder reaction is described. This procedure gives better yields and exhibits better versatility for alkene substrates than the existing hemi‐aminal based methodologies.

Abstract

Synth. Commun. 2008, 38, 803

SULFAMIC ACID AS A NOVEL, EFFICIENT, COST‐EFFECTIVE, AND REUSABLE SOLID ACID CATALYST FOR THE SYNTHESIS OF PYRROLES UNDER SOLVENT‐FREE CONDITIONS

Surya K. De

Burnham Institute for Medical Research, La Jolla, California, USA

Abstract

Synth. Commun. 2008, 38, 810

CONVENIENT SYNTHESIS OF TOLCAPONE, A SELECTIVE CATECHOL‐O‐METHYLTRANSFERASE INHIBITOR

Govindarajan Manikumar, Chunyang Jin, and Kenneth S. Rehder

Organic and Medicinal Chemistry, Science and Engineering Group, Research Triangle Institute, Research Triangle Park, North Carolina, USA

A convenient and efficient synthesis of tolcapone from commercial 4‐benzyloxy‐3‐methoxybenzaldehyde is described. The overall yield is 60%.

Abstract

Synth. Commun. 2008, 38, 816

PRACTICAL SYNTHESIS OF p‐AMINOPHENETHYLSPIPERONE (NAPS), A HIGH‐AFFINITY, SELECTIVE D₂‐DOPAMINE RECEPTOR ANTAGONIST

Chunyang Jin, Louise D. Mayer, Anita H. Lewin, Kenneth S. Rehder, and George A. Brine

Center for Organic and Medicinal Chemistry, RTI International, Research Triangle Park, North Carolina, USA

An improved and efficient approach to the synthesis of multi‐gram amounts of p‐aminophenethylspiperone (NAPS), a high‐affinity and selective D₂‐dopamine reeptor antagonist, is described. Pure NAPS was obtained in 41% overall yield from commercially available 1‐phenyl‐1,3,8‐triazaspiro[4.5]decan‐4‐one.