A novel class of aryl vinyl ethers 3 and diethyl 3-cyano-3-alkylprop-1-en-2-ylphosphonates 4 has ... more A novel class of aryl vinyl ethers 3 and diethyl 3-cyano-3-alkylprop-1-en-2-ylphosphonates 4 has been prepared, respectively, from coupling reaction of diethyl 1-(bromomethyl)-2-cyanovinylphosphonate 2 with phenols and Gilman reagents.
The derivatization of resin-bound aminobenzimidazole toward the parallel solid-phase synthesis of... more The derivatization of resin-bound aminobenzimidazole toward the parallel solid-phase synthesis of aminobenzimidazole tethered pharmacologically important heterocycles such as quinazoline-2,4-diones, thioxoquinazolin-4-ones, benzodiazepine-2,3,5-triones, isoxazoles and isoxazolines is reported. All the compounds were tested for IKK inhibition. Only one compound elicited significant inhibition of IKKε, TBK-1 and IKK2.
The conjugate addition of primary amines in methanol at 0°C to the difunctionalized O-methyl ally... more The conjugate addition of primary amines in methanol at 0°C to the difunctionalized O-methyl allyl ether, prepared from dimethyl a-(bromomethyl)fumarate, provides an adduct which cyclizes via a 5exo-trig process to yield a new family of 3,4-cis-disubstituted pyrrolidin-2-ones in high yields.
Methyl 1-alkyl-4-(diethoxyphosphoryl)-5-oxo-2,5-dihydro-1H-pyrroles-3-carboxylate 4 was synthesiz... more Methyl 1-alkyl-4-(diethoxyphosphoryl)-5-oxo-2,5-dihydro-1H-pyrroles-3-carboxylate 4 was synthesized from the reaction of dimethyl 2-(bromomethyl)-3-(diethoxyphosphoryl) fumarate 3-E and primary amines in good yields.
a b s t r a c t A regioselective coupling of ethyl 2-(bromomethyl)-3-cyanoacrylate and primary am... more a b s t r a c t A regioselective coupling of ethyl 2-(bromomethyl)-3-cyanoacrylate and primary amines is described to give ethyl 2-[(alkylamino)(cyano)methyl] acrylates in good yields. Whereas the conversion of allyl bromide in the presence of TEAF leads to the first synthesis of ethyl 3-cyano-2-(hydroxymethyl) acrylate. Tetrahedron j o u r n a l h o m e p a g e : w w w . e l s e v i e r . c o m / l o c a t e / t e t bromination-dehydrobromination of ethyl 2-(cyanomethyl) acrylate 3 in the presence of triethylamine according to the method published previously 30 (Scheme 3).
ABSTRACT A simple and useful tandem addition–cyclization reaction of primary amines on a prepared... more ABSTRACT A simple and useful tandem addition–cyclization reaction of primary amines on a prepared α-functionalized propylvinyl ketone 3 in methanol at reflux is a promising route for the synthesis of a new family of 1-alkyl-4-propionylpyrrolidin-2-ones 4.[Supplementary materials are available for this article. Go to the publisher's online edition of Synthetic Communications® for the following free supplemental resource(s): Full experimental and spectral details.]
The synthesis of 25,27-dimethoxy-26,28-dimethylacetate-p-tert-butylcalix[4]arene is presented. Co... more The synthesis of 25,27-dimethoxy-26,28-dimethylacetate-p-tert-butylcalix[4]arene is presented. Complexation studies towards alkali metal cations showed selectivities for Na + and Li + . Different conformations for the 1:1 complexes are detected depending on the solvent used. X-ray structures of the ligand and some complexes are given.
A novel class of aryl vinyl ethers 3 and diethyl 3-cyano-3-alkylprop-1-en-2-ylphosphonates 4 has ... more A novel class of aryl vinyl ethers 3 and diethyl 3-cyano-3-alkylprop-1-en-2-ylphosphonates 4 has been prepared, respectively, from coupling reaction of diethyl 1-(bromomethyl)-2-cyanovinylphosphonate 2 with phenols and Gilman reagents.
The derivatization of resin-bound aminobenzimidazole toward the parallel solid-phase synthesis of... more The derivatization of resin-bound aminobenzimidazole toward the parallel solid-phase synthesis of aminobenzimidazole tethered pharmacologically important heterocycles such as quinazoline-2,4-diones, thioxoquinazolin-4-ones, benzodiazepine-2,3,5-triones, isoxazoles and isoxazolines is reported. All the compounds were tested for IKK inhibition. Only one compound elicited significant inhibition of IKKε, TBK-1 and IKK2.
The conjugate addition of primary amines in methanol at 0°C to the difunctionalized O-methyl ally... more The conjugate addition of primary amines in methanol at 0°C to the difunctionalized O-methyl allyl ether, prepared from dimethyl a-(bromomethyl)fumarate, provides an adduct which cyclizes via a 5exo-trig process to yield a new family of 3,4-cis-disubstituted pyrrolidin-2-ones in high yields.
Methyl 1-alkyl-4-(diethoxyphosphoryl)-5-oxo-2,5-dihydro-1H-pyrroles-3-carboxylate 4 was synthesiz... more Methyl 1-alkyl-4-(diethoxyphosphoryl)-5-oxo-2,5-dihydro-1H-pyrroles-3-carboxylate 4 was synthesized from the reaction of dimethyl 2-(bromomethyl)-3-(diethoxyphosphoryl) fumarate 3-E and primary amines in good yields.
a b s t r a c t A regioselective coupling of ethyl 2-(bromomethyl)-3-cyanoacrylate and primary am... more a b s t r a c t A regioselective coupling of ethyl 2-(bromomethyl)-3-cyanoacrylate and primary amines is described to give ethyl 2-[(alkylamino)(cyano)methyl] acrylates in good yields. Whereas the conversion of allyl bromide in the presence of TEAF leads to the first synthesis of ethyl 3-cyano-2-(hydroxymethyl) acrylate. Tetrahedron j o u r n a l h o m e p a g e : w w w . e l s e v i e r . c o m / l o c a t e / t e t bromination-dehydrobromination of ethyl 2-(cyanomethyl) acrylate 3 in the presence of triethylamine according to the method published previously 30 (Scheme 3).
ABSTRACT A simple and useful tandem addition–cyclization reaction of primary amines on a prepared... more ABSTRACT A simple and useful tandem addition–cyclization reaction of primary amines on a prepared α-functionalized propylvinyl ketone 3 in methanol at reflux is a promising route for the synthesis of a new family of 1-alkyl-4-propionylpyrrolidin-2-ones 4.[Supplementary materials are available for this article. Go to the publisher's online edition of Synthetic Communications® for the following free supplemental resource(s): Full experimental and spectral details.]
The synthesis of 25,27-dimethoxy-26,28-dimethylacetate-p-tert-butylcalix[4]arene is presented. Co... more The synthesis of 25,27-dimethoxy-26,28-dimethylacetate-p-tert-butylcalix[4]arene is presented. Complexation studies towards alkali metal cations showed selectivities for Na + and Li + . Different conformations for the 1:1 complexes are detected depending on the solvent used. X-ray structures of the ligand and some complexes are given.
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