Hassen AMRI - Academia.edu (original) (raw)
Papers by Hassen AMRI
Synthetic Communications, 1999
ABSTRACT
Synthetic Communications, Feb 13, 2018
International audienceAn efficient coupling reaction of allyl bromides with various alcohols as n... more International audienceAn efficient coupling reaction of allyl bromides with various alcohols as nucleophiles activated by triethylamine, leading to functionalized vinyl ethers in good yields and with full stereoselectivity
Synthetic Communications, 2014
Abstract We describe a simple and efficient protocol for accessing some unsaturated heterocyclic ... more Abstract We describe a simple and efficient protocol for accessing some unsaturated heterocyclic compounds in a direct evaluation of allyl bromide as Z-ethyl 3-bromomethyl-4-oxopent-2-enoate. The latter reacts with primary amines via two successive nucleophilic substitutions followed by a 5-exo-trig cyclization to produce selectively 4-acetyl-1-alkyl-1H-pyrrol-2(5H)-ones in good yields. GRAPHICAL ABSTRACT
![Research paper thumbnail of ChemInform Abstract: One‐Pot Synthesis of [1,2]Isoxazolidin‐5‐ones and [1,2]Oxazin‐6‐ones](https://attachments.academia-assets.com/116152797/thumbnails/1.jpg)
](ChemInform, 2011
Allyl bromides (I) and (IV) are used as precursors for the synthesis of functionalized [1,2]isoxa... more Allyl bromides (I) and (IV) are used as precursors for the synthesis of functionalized [1,2]isoxazolidin‐5‐ones (III) and [1,2]oxazin‐6‐ones (VI), respectively.
Synthetic Communications, 2013
Phosphorus, Sulfur, and Silicon and the Related Elements, 2010
Ethyl α-cyanoalkyl β-substituted acrylates 5a–i were prepared in good yields on a synthetic scale... more Ethyl α-cyanoalkyl β-substituted acrylates 5a–i were prepared in good yields on a synthetic scale by Horner–Wadsworth–Emmons olefination of the corresponding ethyl 2-(diethoxy-phosphoryl) cyanoalkanoates 3a–c using different aldehydes and anhydrous potassium carbonate in dry THF at reflux
Heteroatom Chemistry, 2013
An easy regio-and stereoselective synthesis of new nitrogenous molecules 2ae was successfully rea... more An easy regio-and stereoselective synthesis of new nitrogenous molecules 2ae was successfully realized via an effective coupling reaction of diethyl (E)-1-(bromomethyl)-2cyanovinylphosphonate 1 with various secondary amines in methanol. Hence, the use of less and more bulky secondary amines gives rise, respectively, to the successive (S N 2) substitution-isomerization and (S N 2) substitution derivatives 2a-c and 2d-e. Moreover, the addition of tertiary amines to 1 in the same reaction conditions, leads exclusively to the rearranged vinyl ether 3 in good yields.
Synthetic Communications, 2004
A convenient stereoselective synthesis of functional homoallylsilanes 2 has been developed by rea... more A convenient stereoselective synthesis of functional homoallylsilanes 2 has been developed by reaction of trimethylsilanylmethylmagnesium chloride on the Baylis–Hillman acetates 1, in anhydrous tetrahydrofuran (THF) in the presence of a catalytic amount of LiCuBr2.
Tetrahedron, 1991
Abstract A new convenient stereoselective synthesis of β-brominated β′-(functional alkyl) α,β-uns... more Abstract A new convenient stereoselective synthesis of β-brominated β′-(functional alkyl) α,β-unsaturated esters has been developed by the reaction of tetraalkylammonium fluoride in HMPA with ethyl 2,3-dibromo 2-(functional alkyl) propionates which can be easily prepared by addition of bromine to β′-(functional alkyl) acrylates. An interpretation of the observed stereoselectivity is proposed.
Bioorganic & Medicinal Chemistry Letters, 2006
Adenophorine and its 5-deoxy analogue have been identified as natural iminosugars with efficient ... more Adenophorine and its 5-deoxy analogue have been identified as natural iminosugars with efficient glycosidase inhibitory effects. The syntheses and biological evaluation of two new series of 5-deoxyadenophorine analogues in their racemic form are reported. The compounds 12e and 13d bearing a C11 and C7 alkyl chain, respectively, were found to be potent inhibitors of the beta-glucosidase from almond with Ki near to 60 microM. The compounds 13a,d which possess a 3,4-cis stereochemistry were efficient on glucosidases but also on the beta-galactosidase, what was not observed with the 3,4-trans series 12.
ChemInform, 2005
Alkyl a-(hydroxymethyl)acrylates are prepared in high yields on a synthetic scale by hydroxymethy... more Alkyl a-(hydroxymethyl)acrylates are prepared in high yields on a synthetic scale by hydroxymethylation of the corresponding acrylates using 30% aqueous formaldehyde in THF or DME as solvent and DABCO as the catalyst.
ChemInform, 2003
First Synthesis of 2-[Alkylamino(diethoxyphosphoryl)methyl]acrylic Ethyl Esters. ... For Abstract... more First Synthesis of 2-[Alkylamino(diethoxyphosphoryl)methyl]acrylic Ethyl Esters. ... For Abstract see ChemInform Abstract in Full Text. ... The first synthesis of title compounds (V) is based on the convenient preparation of the precursor (III) and its S N 2′-type reaction with primary ...
Beilstein journal of organic chemistry, 2005
New α-methylene-γ-nitroketones 5 were synthesized, in fair to good yields, from the coupling reac... more New α-methylene-γ-nitroketones 5 were synthesized, in fair to good yields, from the coupling reaction of a new family of allyl acetates 3 and nitroalkane salts.
An efficient conjugate addition of carbon nucleophiles such as nitronate salts to ethyl 5-cyanocy... more An efficient conjugate addition of carbon nucleophiles such as nitronate salts to ethyl 5-cyanocyclopent-1enecarboxylate 3, produces a variety of 1,2,3-trifunctionalized cyclopentanes 4 in satisfactory yields.
Mediterranean Journal of Chemistry, 2016
An efficient and straightforward approach toward functionalized allylic amines and ethers is disc... more An efficient and straightforward approach toward functionalized allylic amines and ethers is disclosed starting from tetraethyl (3-bromoprop-1-ene-1,2-diyl)bisphosphonate (E)-1 and secondary and tertiary amines. The coupling reaction of allyl bromide (E)-1 with less bulky secondary amines provides a new family of allylamines 3, while, its reaction with more bulky secondary and tertiary amines, in methanol at reflux, led to functional allyl ethers 4 and 5.
Bioorganic & medicinal chemistry letters, 2015
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.
Mediterranean Journal of Chemistry, 2012
This paper describes a convenient synthesis of novel series of 3,4-disubstituted pyrrolidines bas... more This paper describes a convenient synthesis of novel series of 3,4-disubstituted pyrrolidines based on the aza-Michael addition of primary amines to 3,4-difunctionalized-1,3-diene followed by an intramolecular cyclization.
Tetrahedron Letters, 1987
Tetrahedron Letters, 1989
ABSTRACT
Synthetic Communications, 1999
ABSTRACT
Synthetic Communications, Feb 13, 2018
International audienceAn efficient coupling reaction of allyl bromides with various alcohols as n... more International audienceAn efficient coupling reaction of allyl bromides with various alcohols as nucleophiles activated by triethylamine, leading to functionalized vinyl ethers in good yields and with full stereoselectivity
Synthetic Communications, 2014
Abstract We describe a simple and efficient protocol for accessing some unsaturated heterocyclic ... more Abstract We describe a simple and efficient protocol for accessing some unsaturated heterocyclic compounds in a direct evaluation of allyl bromide as Z-ethyl 3-bromomethyl-4-oxopent-2-enoate. The latter reacts with primary amines via two successive nucleophilic substitutions followed by a 5-exo-trig cyclization to produce selectively 4-acetyl-1-alkyl-1H-pyrrol-2(5H)-ones in good yields. GRAPHICAL ABSTRACT
ChemInform, 2011
Allyl bromides (I) and (IV) are used as precursors for the synthesis of functionalized [1,2]isoxa... more Allyl bromides (I) and (IV) are used as precursors for the synthesis of functionalized [1,2]isoxazolidin‐5‐ones (III) and [1,2]oxazin‐6‐ones (VI), respectively.
Synthetic Communications, 2013
Phosphorus, Sulfur, and Silicon and the Related Elements, 2010
Ethyl α-cyanoalkyl β-substituted acrylates 5a–i were prepared in good yields on a synthetic scale... more Ethyl α-cyanoalkyl β-substituted acrylates 5a–i were prepared in good yields on a synthetic scale by Horner–Wadsworth–Emmons olefination of the corresponding ethyl 2-(diethoxy-phosphoryl) cyanoalkanoates 3a–c using different aldehydes and anhydrous potassium carbonate in dry THF at reflux
Heteroatom Chemistry, 2013
An easy regio-and stereoselective synthesis of new nitrogenous molecules 2ae was successfully rea... more An easy regio-and stereoselective synthesis of new nitrogenous molecules 2ae was successfully realized via an effective coupling reaction of diethyl (E)-1-(bromomethyl)-2cyanovinylphosphonate 1 with various secondary amines in methanol. Hence, the use of less and more bulky secondary amines gives rise, respectively, to the successive (S N 2) substitution-isomerization and (S N 2) substitution derivatives 2a-c and 2d-e. Moreover, the addition of tertiary amines to 1 in the same reaction conditions, leads exclusively to the rearranged vinyl ether 3 in good yields.
Synthetic Communications, 2004
A convenient stereoselective synthesis of functional homoallylsilanes 2 has been developed by rea... more A convenient stereoselective synthesis of functional homoallylsilanes 2 has been developed by reaction of trimethylsilanylmethylmagnesium chloride on the Baylis–Hillman acetates 1, in anhydrous tetrahydrofuran (THF) in the presence of a catalytic amount of LiCuBr2.
Tetrahedron, 1991
Abstract A new convenient stereoselective synthesis of β-brominated β′-(functional alkyl) α,β-uns... more Abstract A new convenient stereoselective synthesis of β-brominated β′-(functional alkyl) α,β-unsaturated esters has been developed by the reaction of tetraalkylammonium fluoride in HMPA with ethyl 2,3-dibromo 2-(functional alkyl) propionates which can be easily prepared by addition of bromine to β′-(functional alkyl) acrylates. An interpretation of the observed stereoselectivity is proposed.
Bioorganic & Medicinal Chemistry Letters, 2006
Adenophorine and its 5-deoxy analogue have been identified as natural iminosugars with efficient ... more Adenophorine and its 5-deoxy analogue have been identified as natural iminosugars with efficient glycosidase inhibitory effects. The syntheses and biological evaluation of two new series of 5-deoxyadenophorine analogues in their racemic form are reported. The compounds 12e and 13d bearing a C11 and C7 alkyl chain, respectively, were found to be potent inhibitors of the beta-glucosidase from almond with Ki near to 60 microM. The compounds 13a,d which possess a 3,4-cis stereochemistry were efficient on glucosidases but also on the beta-galactosidase, what was not observed with the 3,4-trans series 12.
ChemInform, 2005
Alkyl a-(hydroxymethyl)acrylates are prepared in high yields on a synthetic scale by hydroxymethy... more Alkyl a-(hydroxymethyl)acrylates are prepared in high yields on a synthetic scale by hydroxymethylation of the corresponding acrylates using 30% aqueous formaldehyde in THF or DME as solvent and DABCO as the catalyst.
ChemInform, 2003
First Synthesis of 2-[Alkylamino(diethoxyphosphoryl)methyl]acrylic Ethyl Esters. ... For Abstract... more First Synthesis of 2-[Alkylamino(diethoxyphosphoryl)methyl]acrylic Ethyl Esters. ... For Abstract see ChemInform Abstract in Full Text. ... The first synthesis of title compounds (V) is based on the convenient preparation of the precursor (III) and its S N 2′-type reaction with primary ...
Beilstein journal of organic chemistry, 2005
New α-methylene-γ-nitroketones 5 were synthesized, in fair to good yields, from the coupling reac... more New α-methylene-γ-nitroketones 5 were synthesized, in fair to good yields, from the coupling reaction of a new family of allyl acetates 3 and nitroalkane salts.
An efficient conjugate addition of carbon nucleophiles such as nitronate salts to ethyl 5-cyanocy... more An efficient conjugate addition of carbon nucleophiles such as nitronate salts to ethyl 5-cyanocyclopent-1enecarboxylate 3, produces a variety of 1,2,3-trifunctionalized cyclopentanes 4 in satisfactory yields.
Mediterranean Journal of Chemistry, 2016
An efficient and straightforward approach toward functionalized allylic amines and ethers is disc... more An efficient and straightforward approach toward functionalized allylic amines and ethers is disclosed starting from tetraethyl (3-bromoprop-1-ene-1,2-diyl)bisphosphonate (E)-1 and secondary and tertiary amines. The coupling reaction of allyl bromide (E)-1 with less bulky secondary amines provides a new family of allylamines 3, while, its reaction with more bulky secondary and tertiary amines, in methanol at reflux, led to functional allyl ethers 4 and 5.
Bioorganic & medicinal chemistry letters, 2015
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.
Mediterranean Journal of Chemistry, 2012
This paper describes a convenient synthesis of novel series of 3,4-disubstituted pyrrolidines bas... more This paper describes a convenient synthesis of novel series of 3,4-disubstituted pyrrolidines based on the aza-Michael addition of primary amines to 3,4-difunctionalized-1,3-diene followed by an intramolecular cyclization.
Tetrahedron Letters, 1987
Tetrahedron Letters, 1989
ABSTRACT