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ANTI – INFECTIVE PYRIDO (1,2 -A) PYRIMIDINES

The present invention relates to small molecule compounds and their use in the treatment of bacterial infections, in particular Tuberculosis

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Oxazolidine – Wikipedia,
Oxazolidine | C3H185NO – PubChem

 

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Nickel catalyzed addition of -NH- containing compounds to vinyl and aryl halides

A process for producing unsaturated nitrogen containing compounds such as enamides, enamines and aryl amines/amides is disclosed. A vinyl halide or aryl halide is reacted with an -NH- containing compound in the presence of a catalytic amount of a catalyst precursor composition comprising zero-valent nickel and an organophosphine ligand. One step coupling of vinyl halides and aryl halides with -NH- containing compounds is made possible by practice of this invention.

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A Highly Regio- and Stereoselective Syntheses of alpha-Halo Enamides, Vinyl Thioethers, and Vinyl Ethers with Aqueous Hydrogen Halide in Two-Phase Systems

A metal-free regio- and stereoselective method is achieved for the preparation of (E)-configured alpha-halo enamides, vinyl thioethers, and vinyl ethers using aqueous HX (X = F, Cl, Br, I), which features high functional group compatibility and regio- and stereoselectivity, mild conditions, high efficiency, and rapid transformation. Additionally, the isomers could be yielded readily from the (E)-configured alpha-halo enamides via photocatalysis or under Sonogashira coupling conditions.

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Oxazolidine – Wikipedia,
Oxazolidine | C3H395NO – PubChem

 

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Advancements in oxazolidinone synthesis utilizing carbon dioxide as a C1 source

Carbon dioxide, a natural molecule, has been utilized in the synthesis of chemicals for several decades. Its innocuous chemical properties make it a favorable substance to incorporate in such synthetic processes. Recently, research is being conducted to include carbon dioxide in the production of a specific class of cyclic urethane molecules known as oxazolidinones. Oxazolidinones are important in synthetic and medicinal applications, which necessitate a greener method to produce them. In this review, various synthetic methods including catalytic processes that incorporate carbon dioxide to yield oxazolidinones have been discussed and the results of the research are presented. Emphasis is placed primarily on reactions of carbon dioxide with a variety of aziridines, propargylamines and 2-amino alcohols for the synthesis of oxazolidinones.

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METHOD FOR PRODUCING 1,4-DIPHENYL AZETIDINONE DERIVATIVES

The present invention is directed to the preparation of novel compounds useful in the treatment of hyperlipidemia, arteriosclerosis, hypercholesterolemia, and other related metabolic disorders. More specifically, the present invention is a novel process for the preparation of 1,4-diphenylazetidinone derivatives from beta-substituted amino amides which are protected in the presence of silylating agents and at least one cyclization catalyst whose structural formula is represented by one of the general formula: Wherein the various R-groups are defined herein

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Copper-catalyzed N-arylation of 2-oxazolidinones. An expeditious route to toloxatone

3-Aryl-2-oxazolidinones are obtained in excellent yields through the copper-catalyzed N-arylation of 2-oxazolidinones with a variety of aryl iodides. With aryl halides containing both iodo and bromo substituents, a high C-I/C-Br selectivity can be achieved. The procedure has been successfully applied to the preparation of a key intermediate in the synthesis of linezolid and to develop an expeditious route to toloxatone.

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Enzyme-assisted asymmetric total synthesis of (-)-podophyllotoxin and (- )-picropodophyllin

Described is the first catalytic, asymmetric synthesis of (-)- podophyllotoxin and its C2-epimer, (-)picropodophyllin. Asymmetry is achieved via the enzymatic desymmetrization of advanced meso diacetate 20, through PPL-mediated ester hydrolysis. A second key feature of the synthesis is the strategically late introduction of the highly oxygenated natural ring E through an arylcopper species. The successful implementation of this approach augers well for the introduction of other functionalized rings E for future SAR work. The synthesis begins from piperonal, which is fashioned into isobenzofuran (IBF) precursor 14 in three steps (bromination, acetalization, and halogenmetal exchange/hydroxymethylation). Interestingly, treatment of 14 with HOAc in commerical dimethyl maleate (contains 5% dimethyl fumarate) leads to a nearly equimolar mixture of fumarate-(15) and maleate-IBF Diels- Alder adducts (16 and 17), indicating that IBF 11 reacts about 15 times faster with dimethyl fumarate than with dimethyl maleate. With scrupulously pure dimethyl maleate a 2.8:1 endo:exo mixture of maleate DA adducts is still obtained. On the other hand, the desired meso diester 16 is obtained pure and in nearly quantitative yield by employing neat dimethyl acetylene dicarboxylate as the dienophile, followed by catalytic hydrogenation. Reduction (LiAlH4) of 16 provides meso diol 19, which is then treated with Ac2O, BzCl, and PhCH2COCl to provide the corresponding meso diesters, 20- 22. Screening of these meso benzoxabicyclo[2.2.1]heptyl substrate candidates across a battery of acyl transfer enzymes leads to an optimized match of diacetate 20 with PPL. Even on 10-20 g scales, asymmetry is efficiently introduced here, yielding the key chiral intermediate, monoacetate 25 (66% isolated yield, 83% corrected yield, 95% ee). Protecting group manipulation and oxidation (Swern) provide aldehyde 27b, which undergoes efficient retro- Michael ring opening to produce dihydronaphthalene 30, in which the C3 and C4 stereocenters are properly set. Following several unsuccessful approaches to the intramolecular delivery of ring E (via Claisen rearrangement, Heck- type cyclization, or radical cyclization), a highly diastereoselective, intermolecular conjugate addition of the arylcopper reagent derived from (3,4,5-trimethoxy)phenylmagnesium bromide and CuCN to acyl oxazolidinone 50 was developed (85% yield, only the required alpha-stereochemistry at C1 is observed). The conjugate addition product is converted to (-)- picropodophyllin in two steps (lactonization, SEM deprotection) or to (-)- podophyllotoxin, in three steps, through the introduction of a C2- epimerization step, under Kende conditions, prior to the final conjugate addition.

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Sustainable Conversion of Carbon Dioxide: An Integrated Review of Catalysis and Life Cycle Assessment

CO2 conversion covers a wide range of possible application areas from fuels to bulk and commodity chemicals and even to specialty products with biological activity such as pharmaceuticals. In the present review, we discuss selected examples in these areas in a combined analysis of the state-of-the-art of synthetic methodologies and processes with their life cycle assessment. Thereby, we attempted to assess the potential to reduce the environmental footprint in these application fields relative to the current petrochemical value chain. This analysis and discussion differs significantly from a viewpoint on CO2 utilization as a measure for global CO2 mitigation. Whereas the latter focuses on reducing the end-of-pipe problem “CO2 emissions” from todays’ industries, the approach taken here tries to identify opportunities by exploiting a novel feedstock that avoids the utilization of fossil resource in transition toward more sustainable future production. Thus, the motivation to develop CO2-based chemistry does not depend primarily on the absolute amount of CO2 emissions that can be remediated by a single technology. Rather, CO2-based chemistry is stimulated by the significance of the relative improvement in carbon balance and other critical factors defining the environmental impact of chemical production in all relevant sectors in accord with the principles of green chemistry.

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Synthesis of Ethylene Glycol from Syngas via Oxidative Double Carbonylation of Ethanol to Diethyl Oxalate and Its Subsequent Hydrogenation

This work reports a novel sustainable two-step method for the synthesis of ethylene glycol (EG) using syngas. In the first step, diethyl oxalate was selectively synthesized via oxidative double carbonylation of ethanol and carbon monoxide (CO) using a ligand-free, recyclable Pd/C catalyst. In the second step, the diethyl oxalate produced underwent subsequent hydrogenation using [2-(di-tert-butylphosphinomethyl)-6-(diethylaminomethyl)pyridine]ruthenium(II) chlorocarbonyl hydride to get EG and ethanol. Thus, the generated ethanol can be recycled back to the first step for double carbonylation. This method gives a sustainable route to manufacture EG using carbon monoxide and hydrogen.

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Cinchona Alkaloid Catalyzed Sulfa-Michael Addition Reactions Leading to Enantiopure beta-Functionalized Cysteines

Sulfa-Michael additions to alpha,beta-unsaturated N-acylated oxazolidin-2-ones and related alpha,beta-unsaturated alpha-amino acid derivatives have been enantioselectively catalyzed by Cinchona alkaloids functionalized with a hydrogen bond donating group at the C6? position. The series of Cinchona alkaloids includes known C6? (thio)urea and sulfonamide derivatives and several novel species with a benzimidazole, squaramide or a benzamide group at the C6? position. The sulfonamides were especially suited as bifunctional organocatalysts as they gave the products in very good diastereoselectivity and high enantioselectivity. In particular, the C6? sulfonamides catalyzed the reaction with the alpha,beta-unsaturated alpha-amino acid derivatives to afford the products in a diastereomeric ratio as good as 93:7, with the major isomer being formed in an ee of up to 99%. The products of the organocatalytic sulfa-Michael addition to alpha,beta-unsaturated alpha-amino acid derivatives were subsequently converted in high yields to enantiopure beta-functionalized cysteines suitable for native chemical ligation.

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