Letters in Organic Chemistry

ISSN: 1570-1786

Letters in Organic Chemistry
Volume 3, Number 2, February 2006

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Highlights in Organic Chemistry

Synthetic Applications of Multi-Component Coupling Reactions Proceeding Via Bis-π-Allylpalladium Complexes Pp. 82-90

Helena C. Malinakova Multi-component coupling reactions proceeding via symmetrical and unsymmetrical bis-π-allylpalladium complexes are reviewed.

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New Developments in Peroxidation of Polyunsaturated Fatty Acids Pp. 91-97

Monica Pierini & Carlo Punta Peroxidation of polyunsaturated fatty acids and atherosclerosis: mechanistic interpretation and recent results on the effects of natural and synthetic antioxidants to prevent chronic diseases.

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Letters in Organic Chemistry

Investigation of the Aqueous Transmetalation of π-Allylpalladium with Indium: Some Theoretical and Experimental Evidence About the Nature of Allylindium Intermediates Pp. 98-102

Gianfranco Fontana, Giuseppe Savona & Francesco Ferrante The nature of the organo-In species involved in the allylation reaction of benzaldehyde with allylic acetates in a mixed acqueous / organic solvent is studied by analizing some experimental and computational evidence.

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Synthesis and Biological Evaluation of a New Benzofuran Analogue of 8-HETE Pp. 103-106

Frederic Caijo, Paul Mosset, Rene Gree, Pascale Chomarat, Valerie Audinot-Bouchez, Jean Boutin, Pierre Renard, Daniel-Henri Caignard & Catherine Dacquet The total synthesis of a 2,3-disubstituted benzofuran, designed as a structural analogue of a bioactive arachidonic acid metabolite, the 8-(S)-HETE, is reported. This heterocyclic derivative has been evaluated as dual agonist of the PPARα and PPARγ nuclear receptors.

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Simple and Recyclable Oxidation, Racemization and Dynamic Kinetic Resolution of Activated Alcohols Catalyzed by Hydrated Ruthenium Chloride in Aqueous Medium Pp. 107-110

Adi Wolfson, Chen Yehuda, Olga Shokin & Dorith Tavor Employing water as medium for aerobic oxidation and dynamic kinetic resolution of activated alcohols with RuCl3, n H2O resulted in simple and recyclable catalytic systems.

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Voltammetric Oxidation of Hantzsch 1,4-Dihydropyridines in Ethanol-Water Media Pp. 111-114

Lida Fotouhi, Shahnaz Khaleghi & Majid M. Heravi The electrochemical oxidation of Hantzsch 1, 4-dihydropyridins (1, 4-DHPs) in the mixture of ethanol-water on carbon electrode is described.

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4H-Thiopyran-1-Oxides. Photochemical Deoxygenation and Oxenoid Reactivity Pp. 115-117

Farnaz Jafarpour & Hooshang Pirelahi The efficient deoxygenation as well as the oxenoid functionalization of solvent as a result of photolysis of some certain non-aromatic sulfoxides, notably 4H-thiopyran-1-oxides are discussed.

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Tetra-n-Propylammonium Perruthenate (TPAP) Catalyzed Aerobic Oxidation of Hydroxylamines to Nitrones Pp. 118-120

Francesca Cardona, Lapo Gorini & Andrea Goti A novel aerobic, environmentally friendly oxidation of hydroxylamines to nitrones catalyzed by tetra-n-propylammonium perruthenate (TPAP) is reported. Complete conversions and reasonable to excellent yields were obtained for cyclic hydroxylamines.

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Solid Phase Regeneration of Carbonyl Compounds by Oxidative Cleavage of Carbon-Nitrogen Double Bonds with Molecular Oxygen at Room Temperature Pp. 121-122

Mohammed M. Hashemi, Maryam Akhbari & Zahed Karimi-Jaberi Montmorillonite K10-supported manganese(II) chloride was found to be an efficient and convenient catalyst for the oxidative cleavage of oximes, phenylhydrazones and semicarbazones to the corresponding carbonyl compounds with molecular oxygen.

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Facile Double Fries Rearrangement of Diesters Under Microwave Irradiation; Application to the Synthesis of a Biogenetically Rare Type of Natural Phenol Pp. 123-127

Firouz Matloubi Moghaddam, Hamdollah Porkaleh & Hassan Zali-Boeini Various diesters successfully undergo a double Fries rearrangement to afford the corresponding bis o-hydroxylaryl ketones, in the presence of AlCl3 under microwave irradiation.

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Design and Synthesis of Spirocyclics Via the Diels-Alder Reaction and Ring-Opening Cross-Metathesis as Key Steps Pp. 128-134

Sambasivarao Kotha, Ashoke Chandra Deb & Subrata Chattopadhyay Ring-opening-cross-metathesis (ROCM) reaction has been used to prepare spiro-indane derivatives containing six rings.

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K2CO3-Mediated Regioselective Synthesis of Isoxazoles and Pyrazolines Pp. 135-139

Mazaahir Kidwai, Shuchi Kukreja & Ruby Thakur 3,5-Diarylisoxazoles and 1,3,5-Triarylpyrazolines are regioselectively synthesised via Michael addition of “hydroxylamine hydrochloride, phenylhydrazine” respectively on chalcones followed by cyclization.

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Stereoselective Total Synthesis of (+)-Sedamine Pp. 140-142

Jagat C. Borah, Joshodeep Boruwa & Nabin C. Barua A stereoselective total synthesis of piperidine alkaloid (+)-sedamine has been described utilizing two regioselective ring-opening reactions of epoxide with vinyl metallic reagent and a ring closing metathesis reaction as the key steps.

The Natural Amino Acid Derived Chiral Sulfonamide Ligands in the Catalytic Asymmetric Addition of Phenylacetylene to Aldehydes Pp. 143-148

Zhi-jian Han, Chao-shan Da, Li Qiu, Ming Ni, Yi-feng Zhou & Rui Wang Several simple amino acids derived chiral sulfonamide ligands were synthesized in simple three steps. When we used these ligands as the catalyst in the asymmetric addition of phenylacetylene to aldehydes, the corresponding propargylic alcohol was achieved with good yields. The highest ee value was up to 99%.

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Green Route to the 2,6-Disubstituted Imidazo[2,1-b]-1,3,4-Thiadiazoles by the Cyclocondensation of α-Bromoacetophenone Derivative and 1,3,4-Thiadiazoles Using Ionic Liquids Pp. 149-152

Mazaahir Kidwai & Shweta Rastogi An eco-friendly synthesis of imidazo[2,1-b]-1,3,4-thiadiazoles using ionic liquid, [bmim]PF6 (1-butyl-3-methylimidazolium hexafluorophosphate) is described.

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An Efficient and Eco-Friendly Procedure for the Synthesis of Hantzsch Ethyl 1,4-Dihydro-2,6-Dimethylpyridine-3,5-Dicarboxylates Under Mild and Green Conditions Pp. 153-156

Mohammad Ali Zolfigol*, Peyman Salehi & Maliheh Safaiee A mixture of ethyl acetoacetate and various aldehydes in the presence of ammonium salts were converted to Hantzsch ethyl 1,4-dihydro-2,6-dimethylpyridine-3,5-dicarboxylate under mild and green conditions with good to excellent yields.

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KF/Al2O3 Mediated Aza-Michael Addition of Indoles to Electron-Deficient Olefins Pp. 157-160

Firouz Matloubi Moghaddam, Ghasem Rezanejade Bardajee & Seyedeh Maryam Dokht Taimoory KF/Al2O3 efficiently catalyzes aza-Michael addition of indoles to a variety of electron-deficient olefins.

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Clean and Facile Condensations Reaction of Indoles and Carbonyl Compounds Under Solvent-Free Conditions Pp. 161-164

Shokoufeh Mehrazma, Najmoddin Azizi & Mohammad R. Saidi A simple, rapid. atom economy and highly efficinet green protocol has been developed for the reactions of indole with carbonyl compounds under solvent free conditions. The attractive features of these procedures are the mild reaction conditions, high conversions, cleaner reaction profiles, inexpensive and environmentally friendly lithuim perchlorate and short reaction times.

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New Vistas in Halogen/Metal Exchange Reactions: The Discrimination Between Seemingly Equal Halogens Pp. 165-169

Frédéric Leroux, Nathalie Nicod, Laurence Bonnafoux, Bérengère Quissac & Françoise Colobert Regioselective halogen/lithium permutation reactions were carried out on polybrominated biaryls. Thus, highly functionalized, dissymetrically substituted biaryls become easily accessible on gram scale.

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