MILD AND EFFICIENT METHOD FOR OXIDATION OF ALCOHOLS IN IONIC LIQUID MEDIA

In this study the strong oxidative agent, potassium permanganate, has been moderated with using under ionic liquid media for selective oxidation of some benzylic and aliphatic alcohols to their corresponding carbonyl compounds under mild and green conditions. 1-Butyl-3-methylimidazoliumbromide ([bmim]Br) (BMIM) associated with acetonitrile has been employed as modified media for oxidation of benzylic alcohols. This chemoselective and efficient process produced aldehydes and ketones with higher purity and yields and shorter reaction period in [bmim]Br as ionic liquid than conventional solvents

Solid State Deprotection of Acetals and Thioacetals Using Benzyltriphenylphosphonium Peroxymonosulfate

A variety of acetals and thioacetals 2 are deprotected to the corresponding parent carbonyl compounds 3 under solvent-free conditions using benzyltriphenylphosphonium peroxymonosulfate (1) in the presence of aluminum chloride

Asymmetric synthesis of chiral amines and benzazepine alkaloids from chiral sulfoxides

This thesis investigates the application of chiral sulfoxides to the asymmetric synthesis of chiral amines and benzazepine alkaloids, the results are presented in four chapters. In Chapter 1, the addition of the anions of methyl phenyl sulfoxide and the novel methyl 2-methoxy-l-naphthyl sulfoxide to nitrones was shown to be a diastereoselective process under kinetically controlled conditions. The stereochemistry of these adducts was determine by chemical correlation with known p-amino sulfoxides. Chapter 2 is an extension of this method and describes the addition of lithiated methyl phenyl sulfoxide to oxaziridines. The relative stereochemistry of the major and minor adducts from these reactions was determined by 1H NMR spectroscopic analysis. A new method for the synthesis of oxaziridines by the oxidation of imines with Oxone® is also reported. In Chapter 3, an attempt was made to extend this methodology to the synthesis of β-amino sulfoxide (7), from the addition of methyl phenyl sulfoxide to nitrile oxides, benzohydroximinoyl chlorides and nitriles, and then reduction of the products by either sodium triacetoxyborohydride or sodium cyanoborohydride. However the diastereoselection of these reductions was poor. Chapter 4 deals with an attempt to solve the problems encountered with the synthesis of β-amino sulfoxide (2) in Chapters 1, 2, and 3. β-Keto 2- methoxy-1-naphthyl sulfoxides (1) were prepared and converted to β-amino sulfoxide (2) via a number of methods. These methods included reductive alkylation of (1) and the conversion of (1) to its β-sulfinyl enamine followed by diastereoselective reduction. Attempts to use the β-amino sulfoxide (2) for the synthesis of benzazepine alkaloids via a Pummerer type cyclization failed to give the expected product, however a novel rearrangement product was isolated and characterized

A rapid and convenient synthesis of amides from aromatic acids and aliphatic amines in dry media under microwave irradiation

504-507The synthesis of amides 2 from the corresponding aromatic acids and aliphatic amines in the presence of catalytic amount of p-toluenesulfonic acid has been reported. The reactions are accelerated with microwave irradiation under solvent-free conditions to afford a high yielding synthesis of amides

Highly diastereoselective synthesis and easy method for synthesis of optically active sulfinate esters from aromatic disulfides

536-538One-step synthesis of chiral aromatic sulfinate esters 2 from aromatic disulfides 1 using lead tetraacetate is reported. The yields are good to excellent and diastereoselectivity is high

A new facile and rapid synthesis of acyl azides under solvent-free conditions

1234-1235A rapid and simple method for the preparation of acyl azides is described. The reaction is carried out under solvent-free conditions from the reaction of acid chlorides with sodium azide supported on silica gel. </span

Microwave-assisted rapid synthesis of phthalimide derivatives

250-251A simple, extremely fast, and high yielding method for the reaction of phthalic anhydride with a number of amino acids using microwave irradiation under solventless 'dry' conditions has been developed. The phthalimide derivatives are prepared in excellent yields and without racemization

1-Benzyl-1-azonia-4-azabicyclo[2.2.2]octane tetrahydroborate (BAAOTB) as a selective reducing agent

239-2421-Benzyl-1-azonia-4-azabicyclo[2.2.2]octane tetrahydroborate (BAAOTB) 1 generated as white solid from commercially available DABCO and sodium borohydride is found to be a selective and versatile reducing agent. The reagent in t-butanol is very useful for reduction of imines, enamines, oximes, reductive amination of aldehydes and ketones and reductive methylation of amines.</span

Solid-state Synthesis of 1-Ethoxycarbonyl-4-substituted-semicarbazides

A rapid and simple method for the preparation of 1-ethoxycarbonyl-4-substituted-semicarbazides has been developed. As examples the reaction of six different isocyanates with ethyl carbazate under solvent-free conditions are reported