0000000001301688

AUTHOR

Saoussen Haddad

showing 6 related works from this author

Regio- and Stereoselective Synthesis of Spiropyrrolizidines and Piperazines through Azomethine Ylide Cycloaddition Reaction.

2015

A series of original spiropyrrolizidine derivatives has been prepared by a one-pot three-component [3 + 2] cycloaddition reaction of (E)-3-arylidene-1-phenyl-pyrrolidine-2,5-diones, l-proline, and the cyclic ketones 1H-indole-2,3-dione (isatin), indenoquinoxaline-11-one and acenaphthenequinone. We disclose an unprecedented isomerization of some spiroadducts leading to a new family of spirooxindolepyrrolizidines. Furthermore, these cycloadducts underwent retro-1,3-dipolar cycloaddition yielding unexpected regioisomers. Upon treatment of the dipolarophiles with in situ generated azomethine ylides from l-proline or acenaphthenequinone, formation of spiroadducts and unusual polycyclic fused pip…

IsatinThiosemicarbazonesStereochemistryAzomethine ylideStereoisomerism010402 general chemistry01 natural sciencesPiperazineschemistry.chemical_compoundX-Ray DiffractionStructural isomerSpiro CompoundsComputingMilieux_MISCELLANEOUSPyrrolizidine AlkaloidsCycloaddition Reaction010405 organic chemistryHydrogen bondIsatinOrganic ChemistryStereoisomerismCycloaddition0104 chemical sciencesKineticschemistryCyclizationQuantum TheoryStereoselectivity[PHYS.ASTR]Physics [physics]/Astrophysics [astro-ph]IsomerizationAzo CompoundsThe Journal of organic chemistry
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ChemInform Abstract: Regio- and Stereoselective Synthesis of Spiropyrrolizidines and Piperazines Through Azomethine Ylide Cycloaddition Reaction.

2016

A series of original spiropyrrolizidine derivatives has been prepared by a one-pot three-component [3 + 2] cycloaddition reaction of (E)-3-arylidene-1-phenyl-pyrrolidine-2,5-diones, l-proline, and the cyclic ketones 1H-indole-2,3-dione (isatin), indenoquinoxaline-11-one and acenaphthenequinone. We disclose an unprecedented isomerization of some spiroadducts leading to a new family of spirooxindolepyrrolizidines. Furthermore, these cycloadducts underwent retro-1,3-dipolar cycloaddition yielding unexpected regioisomers. Upon treatment of the dipolarophiles with in situ generated azomethine ylides from l-proline or acenaphthenequinone, formation of spiroadducts and unusual polycyclic fused pip…

chemistry.chemical_compoundHydrogen bondChemistryIsatinStructural isomerAzomethine ylideStereoselectivityGeneral MedicineMedicinal chemistryIsomerizationCycloadditionChemInform
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CCDC 1405446: Experimental Crystal Structure Determination

2015

Related Article: Saoussen Haddad, Sarra Boudriga, François Porzio, Armand Soldera, Moheddine Askri, Michael Knorr, Yoann Rousselin, Marek M. Kubicki, Christopher Golz, and Carsten Strohmann|2015|J.Org.Chem.|80|9064|doi:10.1021/acs.joc.5b01399

Space GroupCrystallographyCrystal SystemCrystal StructureCell Parameters1'-(4-fluorophenyl)-1''-phenyl-5'6'7'7a'-tetrahydro-1'H2''H5''H-dispiro[indole-33'-pyrrolizine-2'3''-pyrrolidine]-22''5''(1H)-trioneExperimental 3D Coordinates
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CCDC 1405448: Experimental Crystal Structure Determination

2015

Related Article: Saoussen Haddad, Sarra Boudriga, François Porzio, Armand Soldera, Moheddine Askri, Michael Knorr, Yoann Rousselin, Marek M. Kubicki, Christopher Golz, and Carsten Strohmann|2015|J.Org.Chem.|80|9064|doi:10.1021/acs.joc.5b01399

Space GroupCrystallographyCrystal System1'-(4-chlorophenyl)-1''-phenyl-5'6'7'7a'-tetrahydro-1'H2''H5''H-dispiro[indole-33'-pyrrolizine-2'3''-pyrrolidine]-22''5''(1H)-trioneCrystal StructureCell ParametersExperimental 3D Coordinates
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CCDC 1405449: Experimental Crystal Structure Determination

2015

Related Article: Saoussen Haddad, Sarra Boudriga, François Porzio, Armand Soldera, Moheddine Askri, Michael Knorr, Yoann Rousselin, Marek M. Kubicki, Christopher Golz, and Carsten Strohmann|2015|J.Org.Chem.|80|9064|doi:10.1021/acs.joc.5b01399

Space GroupCrystallography1'2'3'8'9'10'10a'10b'-octahydro-2H2''H-dispiro[acenaphthylene-15'-dipyrrolo[12-a:2'1'-c]pyrazine-6'1''-acenaphthylene]-22''-dioneCrystal SystemCrystal StructureCell ParametersExperimental 3D Coordinates
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CCDC 1405447: Experimental Crystal Structure Determination

2015

Related Article: Saoussen Haddad, Sarra Boudriga, François Porzio, Armand Soldera, Moheddine Askri, Michael Knorr, Yoann Rousselin, Marek M. Kubicki, Christopher Golz, and Carsten Strohmann|2015|J.Org.Chem.|80|9064|doi:10.1021/acs.joc.5b01399

Space GroupCrystallography2'-(4-chlorophenyl)-1''-phenyl-5'6'7'7a'-tetrahydro-2''H5''H-dispiro[indole-33'-pyrrolizine-1'3''-pyrrolidine]-22''5''(1H)-trioneCrystal SystemCrystal StructureCell ParametersExperimental 3D Coordinates
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