Search results for "DISCOVERY"

Cycloaddition reactions of benzothiete and hetero dienophiles for the synthesis of heterocyclic systems

1986

Abstract Benzothiete ( 1 ) undergoes cycloaddition reactions with hetero dienophiles with NN-, NO- or CO- double bonds, leading to six-membered heterocyclic ring systems of 2H-3,4-dihydro-1,2,3-benzothiadiazine ( 3 ), 4H-3,1,2-benzoxathiazine ( 4 ) and 4H-3,1-benzoxathiin.

Evidence of a 1,4-dipole intermediate in the reaction of 1-phenyl-4-vinylpyrazole with ptad

1985

Abstract 1-Phenyl-4-vinylpyrazole reacts with 1-phenyl-1,2,4-triazoline-3,5-dione in methylene chloride to form an unstable azetidine (4). An intermediate 1,4-dipole is probably involved since, when the reaction is conducted in acetone, a 1:1:1 adduct (3) is isolated.

A non-catalyzed ring-opening aminolysis reaction of sesquiterpene lactones

1994

Abstract Santonin (1) and other sesquiterpene lactones (6–10) react cleanly with pyrrolidine at room temperature to afford γ-hydroxyalkylamides, which by elimination with mesyl chloride in pyridine-benzene at 80°C give unsaturated alkylamides.

Structure and fluxional behaviour of heptaleneirontricarbonyl and heptalenebis (Irontricarbonyl)

1987

Abstract The synthesis of heptaleneirontricarbonyl ( 4 ) is described. The structures of 4 and of the closely related heptalenebis(irontricarbonyl) ( 3 ) are elucidated by NMR spectroscopy ( 1H and 13C) and by X-ray crystallography. Compounds 3 and 4 are shown by dynamic NMR to undergo an isodynamic 1 ,2-migration of the Fe(CO3)-groups as well as a carbonyl scrambling. The relevant kinetic data allow for a mechanistic discussion of the dynamics and a comparison with other irontricarbonyl complexes.

Synthesis of two natural 8-oxo-β-cyperone derivatives from (−)-santonin.

1993

Abstract This paper reports on the chemical transformations of (−)-santonin into (+)-8-oxo-β-cyperone and (+)-12-hydroxy-8-oxo-β-cyperone involving 8-oxo group introduction and elaboration of the side chain.

Total synthesis of (−)-mintlactone

1991

Abstract The first total, stereodirected synthesis of (—)-mintlactone is described. A stereoselective, radical-mediated ring closure was the key step in the synthesis.

Frontispiece: Tailor‐Made Amino Acids and Fluorinated Motifs as Prominent Traits in Modern Pharmaceuticals

2020

Straightforward synthesis of bioconjugatable azo dyes. Part 2: Black Hole Quencher-2 (BHQ-2) and BlackBerry Quencher 650 (BBQ-650) scaffolds

2014

Abstract A further extension of the efficient synthetic methodology described in Part 1, to the aromatic bis-diazo scaffold of Black Hole Quencher-2 dye is presented. Bioconjugatable derivatives bearing either azido, terminal alkyne, or maleimide reactive group were easily obtained as well as the free-phenol form of BlackBerry® Quencher 650 (BBQ-650®) initially developed by Berry & Associates, Inc. Company. The efficient conjugation ability of azido- and maleimide-quenchers was demonstrated through the facile preparation of the first water-soluble and formylated BHQ-2 dyes and a FRET-based probe suitable for the in vitro/in cellulo detection of a cancer-associated protease namely urokinase-…

A Novel Series of 2-Carboxytetrahydroquinolines Provides New Insights into the Eastern Region of Glycine Site NMDA Antagonists

2000

A series of potent 4-substituted tetrahydroquinolines has been synthesized and biologically tested in order to refine the eastern region of the pharmacophore model for glycine site NMDA antagonists concerning the assessment of lipophilicity, flexibility, and hydrogen bonding. Displacement studies on rat cortical membranes using [ 3 H]-5,7-dichlorokynurenic acid as a radioligand indicated that binding affinities are markedly enhanced when additional hydrogen-accepting groups are introduced into the eastern region of the 2-carboxytetrahydroquinolines. Among the most potent ligands were some urea, sulfonylurea, and crown ether compounds as interesting leads for new diagnostics, especially for …

Stereoselektive c-glycosidsynthese durch titan-(iv)-katalysierte addition von silylenolethern an 2-acyloxy-3-keto-glycale

1984

Abstract C-Glycosides are stereoselectively formed by the titan-(IV)-catalysed addition of silyl enolethers 2 to 2,4,6-tri-O-acyl-1-deoxy-D-erythro-hex-1-enopyran-3-uloses 1 followed by elimination of the 4-acyloxy substituent. Cyclohexenyl silylether 2a reacts with 2-acetoxy-3-keto-glycal derivative la forming only one product 3a . Thus, the reaction seems to be diastereospecific with respect to both new chiral centers of the product.