129097-92-3

Upstream product

• 74213-24-4 N-dibromomethylidenehydroxylamine 
• 107-18-6 allyl alcohol 
• 13146-23-1 copper(I) phenylacetylenide 

Downstream Products

• 128993-18-0 (5R)-3-Bromo-5-hydroxymethyl-Δ²-isoxazoline 
• 128993-17-9 (5S)-3-Bromo-5-hydroxymethyl-Δ²-isoxazoline 
• 918440-90-1 ((S)-3-bromo-4,5-dihydroisoxazol-5-yl)methyl acetate 
• 83527-35-9 S-3,4-dihydroxy butyronitrile 
• 128993-09-9 (RS)-3-benzyloxy-5-(hydroxymethyl)-Δ²-isoxazoline 
• 152611-10-4 (S)-2-Cyclohexyl-5-hydroxymethyl-isoxazolidin-3-one 
• 140384-88-9 Butyric acid (R)-3-bromo-4,5-dihydro-isoxazol-5-ylmethyl ester 
• 140384-87-8 Butyric acid (S)-3-bromo-4,5-dihydro-isoxazol-5-ylmethyl ester 

Relevant academic research and scientific papers

Palladium-free Sonogashira-type cross-coupling reaction of bromoisoxazolines or N-alkoxyimidoyl bromides and alkynes

A Cu(I)-catalysed Sonogashira-type cross coupling reaction with aliphatic or aromatic bromoisoxazolines or N-alkoxyimidoyl bromides and alkynes is reported. The protocol we developed employs catalytic amount of copper(I), non-toxic ligand bathophenanthroline and is tolerant to a wide range of functional groups and is therefore particulary adapted in the context of drug discovery.

Tandem synthesis of 3-halo-5-substituted isoxazoles from 1-copper(I) alkynes and dihaloformaldoximes

A tandem synthesis of 3-halo-5-substituted isoxazoles has been developed from 1-copper(I) alkynes and dihaloformaldoximes under base-free conditions. Thus, 1,3-dipolar cycloaddition and all its drawbacks can now be avoided completely.

The biological targets of acivicin inspired 3-chloro- and 3-bromodihydroisoxazole scaffolds

Target analysis of acivicin derived 3-halodihydroisoxazoles scaffolds in living non-pathogenic and pathogenic bacteria.

BIFUNCTIONAL HETEROCYCLIC COMPOUNDS AND METHODS OF MAKING AND USING SAME

The invention provides a family of bifunctional heterocyclic compounds useful as anti-infective, anti-proliferative, anti-inflammatory, and prokinetic agents. The invention also provides methods of making the bifunctional hetercyclic compounds, and methods of using such compounds as anti-infective, anti-proliferative agents, anti-inflammatory, and/or prokinetic agents.

BROMONITRILE OXIDE CYCLOADDITIONS IN WATER

Bromonitrile oxide can be generated homogeneously in water at acidic pH, allowing efficient cycloaddition with water soluble olefins and acetylenes.Allylammonium salts react with high regioselectivity and without the need for N-group protection. Keyword: Acivicin; transglutaminase; cysteine; 4,5-dihydroisoxazole; dibromonoformaldoxime.

NITRILE OXIDES IN MEDICINAL CHEMISTRY-- 2. SYNTHESIS OF THE TWO ENANTIOMERS OF DIHYDROMUSCIMOL

The cycloaddition of bromonitrile oxide to monosubstituted olefins has a high regioselectivity yielding 3-bomo-5-substituted isoxazolines contaminated by minor amounts (4-9percent) of the 4-substituted isomer.The adducts of bromonitrile oxide to allyl alcohol and N-protected allylamine were employed as key intermediates in the preparation of racemic dihydromuscimol (DHM).The synthesis of (R)-(-)- and (S)-(+)-DHM was accomplished by using the two diastereomers obtained by the cycloaddition of bromonitrile oxide to (S)-(+)-isopropylidene-3-buten-1,2-diol.The enantiomeric excess of R)-(-)- and (S)-(+)-DHM, determined by capillary GLC on the appropriate precursors, were 98.8 and >99.0 percent.A spectroscopic survey of the tautomerism of 3-hydroxyisoxazolines indicates the predominant or exclusive occurence of the NH form.

Synthesis and pharmacological investigation of cholinergic ligands structurally related to muscarone

Five new analogs of muscarone were synthesized in order to evulate the influence of the carbonyl group on muscarinic activity.We chose to introduce structural variations at the C-2 and C-3 positions of the tetrahydrofuran ring.The muscarinic activity was evaluated in vitro on guinea pig atria and ileum as well as on rat jejunum and urinary bladder.All the new derivatives are less potent than muscarone and three of them displayed a potency very close to that previously reported for muscarine.The tissue selectivity observed for the 3-methylene derivative which is eight times more potent on guinea pig ileum than atria is worth noting.The present data show the lack of a simple relationship between the polarity of the group located in the 3-position of the ring and the muscarinic activity.

CONVERSION OF ISOXAZOLINES TO β-HYDROXY ESTERS. SYNTHESIS OF 2-DEOXY-D-RIBOSE

A simple and efficient preparation of β-hydroxy esters with a well-defined stereochemistry has been developed using 3-bromoisoxazolines as key-intermediates.A synthesis of 2-deoxy-D-ribose is also reported.