Hassen AMRI | University of Tunis El Manar (original) (raw)
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Centre National de la Recherche Scientifique / French National Centre for Scientific Research
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![Research paper thumbnail of A practical synthesis of diethyl 1-[(alkylamino)(cyano)methyl]vinylphosphonates](https://attachments.academia-assets.com/86654707/thumbnails/1.jpg)
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The conversion of cyclic Baylis-Hillman acetates 1 into the corresponding cyano derivatives 2 was... more The conversion of cyclic Baylis-Hillman acetates 1 into the corresponding cyano derivatives 2 was achieved using potassium cyanide in the presence of 1,4-diazabicyclo-[2.2.2]octane (DABCO) in aqueous medium. The obtained Michael acceptors 2 easily add primary amines in absolute ethanol to produce a new family of 1,2,3-trisubstituted cyclpentanes 3 in good yields.
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.
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. C 2013 Wiley Periodicals, Inc. Heteroatom Chem. 24:460-465, 2013; View this article online at wileyonlinelibrary.com.
A simple and useful tandem addition-cyclization reaction of primary amines on a prepared a-functi... more A simple and useful tandem addition-cyclization reaction of primary amines on a prepared a-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.
A simple, convenient and highly stereoselective synthesis of diethyl (E)-1-(bromomethyl)-2cyanovi... more A simple, convenient and highly stereoselective synthesis of diethyl (E)-1-(bromomethyl)-2cyanovinylphosphonate 4 is described. The product would be a useful substrate for the synthesis of diethyl 1-[(alkylamino)(cyano)methyl]vinylphosphonates 5 via allylic rearrangement S N 2΄-type mechanism. Scheme 1. Retrosynthetic analysis.
The conversion of cyclic Baylis-Hillman acetates 1 into the corresponding cyano derivatives 2 was... more The conversion of cyclic Baylis-Hillman acetates 1 into the corresponding cyano derivatives 2 was achieved using potassium cyanide in the presence of 1,4-diazabicyclo-[2.2.2]octane (DABCO) in aqueous medium. The obtained Michael acceptors 2 easily add primary amines in absolute ethanol to produce a new family of 1,2,3-trisubstituted cyclpentanes 3 in good yields.
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.
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. C 2013 Wiley Periodicals, Inc. Heteroatom Chem. 24:460-465, 2013; View this article online at wileyonlinelibrary.com.
A simple and useful tandem addition-cyclization reaction of primary amines on a prepared a-functi... more A simple and useful tandem addition-cyclization reaction of primary amines on a prepared a-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.
A simple, convenient and highly stereoselective synthesis of diethyl (E)-1-(bromomethyl)-2cyanovi... more A simple, convenient and highly stereoselective synthesis of diethyl (E)-1-(bromomethyl)-2cyanovinylphosphonate 4 is described. The product would be a useful substrate for the synthesis of diethyl 1-[(alkylamino)(cyano)methyl]vinylphosphonates 5 via allylic rearrangement S N 2΄-type mechanism. Scheme 1. Retrosynthetic analysis.