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Selective preparation of isomers and enantiomers of cyclopropane carboxylic acids

A process has been discovered for selective preparation of isomers and enantiomers of 2,2-dimethyl-3-(2,2-dihalovinyl)cyclopropane carboxylic acids. In this process an adduct of an alkyl 3,3-dimethyl-4-pentenoate and a substituted 2-oxazolidone is reacted with a substituted dihalomethane compound. The resulting compound is cyclized, dehydrohalogenated and hydrolyzed to yield the desired product. These cyclopropane carboxylic acids are useful precursors for pyrethroid insecticides.

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Reference:
Oxazolidine – Wikipedia,
Oxazolidine | C3H144NO – PubChem

 

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Remote, Late-Stage Oxidation of Aliphatic C-H Bonds in Amide-Containing Molecules

Amide-containing molecules are ubiquitous in natural products, pharmaceuticals, and materials science. Due to their intermediate electron-richness, they are not amenable to any of the previously developed N-protection strategies known to enable remote aliphatic C-H oxidations. Using information gleaned from a systematic study of the main features that makes remote oxidations of amides in peptide settings possible, we developed an imidate salt protecting strategy that employs methyl trifluoromethanesulfonate as a reversible alkylating agent. The imidate salt strategy enables, for the first time, remote, nondirected, site-selective C(sp3)-H oxidation with Fe(PDP) and Fe(CF3PDP) catalysis in the presence of a broad scope of tertiary amides, anilide, 2-pyridone, and carbamate functionality. Secondary and primary amides can be masked as N-Ns amides to undergo remote oxidation. This novel imidate strategy facilitates late-stage oxidations in a broader scope of medicinally important molecules and may find use in other C-H oxidations and metal-mediated reactions that do not tolerate amide functionality.

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Reference:
Oxazolidine – Wikipedia,
Oxazolidine | C3H855NO – PubChem

 

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Stereoselective oxindole synthesis by palladium-catalyzed cyclization reaction of 2-(alkynyl)aryl isocyanates with amides

A new cyclization reaction occurred on treatment of 2-(alkynyl)aryl isocyanates with amides in the presence of a palladium(0)/diphosphine catalyst to stereoselectively form 3-(amidoalkylidene)oxindoles. A carbon-nitrogen bond as well as a carbon-carbon bond were simultaneously introduced onto the alkyne moiety to construct an oxindole skeleton with stereoselective placement of the amino substituent cis to the carbonyl group.

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Reference:
Oxazolidine – Wikipedia,
Oxazolidine | C3H822NO – PubChem

 

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Loss of the tert-butyloxycarbonyl (Boc) protecting group under basic conditions

Reaction of 3, the N-Boc, O-tosyl derivative of phenylalaninol, with base leads to loss of the Boc and tosyl groups and formation of oxazolidinone 9. Similar reactions have also been examined. A mechanism to explain loss of the Boc group under basic reaction conditions is proposed.

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Reference:
Oxazolidine – Wikipedia,
Oxazolidine | C3H460NO – PubChem

 

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Recent advances in synthesis of functionalized beta-lactams through cyclization of N-propargyl amine/amide derivatives

beta-lactams have attracted a significant attention due to their potential biological activities and wide variety of synthetic applications. Developing novel and efficient methods for construction of functionalized beta-lactams has been the subject of a number of papers in recent years. N-Propargyl amines/amides are one of the most specific class of alkynes having diverse reaction patterns. It is well known that they can undergo a number of cyclization reactions to produce various significant nitrogen containing heterocycles. This review surveys literature methods for the synthesis of highly substituted beta-lactams from simple and easily available N-propargyl amine/amide derivatives from 1991 to 2017.

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Reference:
Oxazolidine – Wikipedia,
Oxazolidine | C3H1088NO – PubChem

 

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IMIDAZOPYRAZINES AS LSD1 INHIBITORS

The present invention is directed to imidazo[1,2-a]pyrazine derivatives which are LSD1 inhibitors useful in the treatment of diseases such as cancer.

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Reference:
Oxazolidine – Wikipedia,
Oxazolidine | C3H252NO – PubChem

 

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A practical and effective ruthenium trichloride-based protocol for the regio- and stereoselective catalytic hydroamidation of terminal alkynes

A rational catalyst development based on mechanistic and spectroscopic investigations led to the discovery of a new protocol for catalytic hydroamidation reactions that draws on easily available ruthenium trichloride trihydrate (RuCl3·3H2O) as the catalyst precursor instead of the previously employed, expensive bis(2-methylallyl)(1,5- cyclooctadiene) ruthenium(II). This practical and easy-to-use protocol dramatically improves the synthetic applicability of Ru-catalyzed hydroamidations. The catalyst, generated in situ from ruthenium(III) chloride hydrate, tri-n-butylphosphine, 4-(dimethylamino)-pyridine and potassium carbonate, effectively promotes the addition of secondary amides, lactams and carbamates to terminal alkynes under formation of (E)-anti-Markovnikov enamides. The scope of the new protocol is demonstrated by the synthesis of 24 functionalized enamide derivatives, among them valuable intermediates for organic synthesis.

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Reference:
Oxazolidine – Wikipedia,
Oxazolidine | C3H563NO – PubChem

 

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Ligand-Enabled Gold-Catalyzed C(sp2)-N Cross-Coupling Reactions of Aryl Iodides with Amines

The first example of ancillary (P,N)-ligand-enabled gold-catalyzed C-N cross-coupling reactions of aryl iodides with amines is reported. The high generality of the reaction in de novo synthesis, late-stage modifications, and cascade processes to access functionalized indolinones and carbazoles underscores the synthetic potential of the presented strategy. Monitoring the reaction with ESI-HRMS and NMR provided strong evidence for the in situ formation of putative high valent Au(III) intermediates.

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Reference:
Oxazolidine – Wikipedia,
Oxazolidine | C3H281NO – PubChem

 

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A practical ruthenium-catalyzed cleavage of the allyl protecting group in amides, lactams, imides, and congeners

A convenient methodology for the deprotection of N-allylic amide-like moieties was developed. The first examples accounting for the ruthenium-catalyzed deallylation of amides, lactams, imides, pyrazolidones, hydantoins, and oxazolidinones have been achieved by the sequential use of Grubbs carbene (isomerization step) and RuCl3 (oxidation step). A variety of substrates, including enantiopure multifunctional beta- and gamma-lactams, can be employed.

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Reference:
Oxazolidine – Wikipedia,
Oxazolidine | C3H283NO – PubChem

 

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Discovery of novel benzoxazinones as potent and orally active long chain fatty acid elongase 6 inhibitors

A series of benzoxazinones was synthesized and evaluated as novel long chain fatty acid elongase 6 (ELOVL6) inhibitors. Exploration of the SAR of the UHTS lead 1a led to the identification of (S)-1y that possesses a unique chiral quarternary center and a pyrazole ring as critical pharmacophore elements. Compound (S)-1y showed potent and selective inhibitory activity toward human ELOVL6 while displaying potent inhibitory activity toward both mouse ELOVL3 and 6 enzymes. Compound (S)-1y showed acceptable pharmacokinetic profiles after oral dosing in mice. Furthermore, (S)-1y significantly suppressed the elongation of target fatty acids in mouse liver at 30 mg/kg oral dosing. 2009 American Chemical Society.

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Reference:
Oxazolidine – Wikipedia,
Oxazolidine | C3H825NO – PubChem