0000000001299880
AUTHOR
Moheddine Askri
Regioselective Synthesis of Mono- and Dispiropyrazoline Derivatives via 1,3-dipolar Cycloaddition with Nitrilimines
The 1,3-dipolar cycloaddition reaction of (E,E)-1,3-bis(arylidene)indan-2-one with diarylnitrilimines, generated in situ via dehydrohalogenation of the corresponding hydrazonoyl chlorides , affords predominantly monospiropyrazolines and as a mixture of diastereoisomers. Also dispiropyrazolines are formed in moderate yields. The structure and stereochemistry of cycloadducts were confirmed by 1H and 13C-NMR spectroscopy, elemental analyses data, and single-crystal X-ray diffraction studies of and .
Synthesis of highly substituted spiropyrrolidines via 1, 3-dipolar cycloaddition reaction of N-metalated azomethine ylides. A new access to spiropyrroline derivatives
1,3-dipolar cycloaddition of (E)-arylidene-(2H)-indanones 1 (Ar = Ph, p-MeC6H4, p-MeOC6H4, p-ClC6H4) and (E)-2-arylidene-(2H)-tetralones 2 (Ar = Ph, p-MeC6H4, p-MeOC6H4, p-ClC6H4) to N-metalated azomethine ylides 3 generated from methyl N-arylideneglycinate in the presence of silver acetate produces in good yields novel spiro[3,5-(diaryl)-2-carbomethoxypyrrolidine-4:2’-indanones] 4 and spiro[3,5-(diaryl)-2-carbomethoxypyrrolidine-4:2’-tetral-1-ones] 5. The cycloaddition proceeds in regio- and stereoselective manner (100%) at room temperature to afford respectively the syn-endo cycloadducts 4 and 5 via metallo-azomethine ylides. The regio- and stereochemistry of the spiranic adducts has been…
Bis(4-methylthio)phenylthiomethane as assembling ligand for the construction of Cu(I) and Hg(II) coordination polymers. Crystal structures and topological (AIM) analysis of the bonding
International audience; The novel 1D coordination polymer (CP) [{Cu(mu(2)-Br)(2)Cu}(mu-L2)(2)] CP2 has been obtained by reaction of the tetrakisthioether p-MeSC6H4SCH2SC6H4SMe-p (L2) with CuBr in a 1: 2 metal-to ligand ratio. In contrast to the previously described CP [{Cu(mu(2)-Br)(2)Cu}(mu-L1)(2)] CP1 obtained by reaction of the tetrakisthioether p-MeOC6H4SCH2SC6H4OMe-p (L1) with CuBr, the two independent extended 1D ribbons contain bent Cu(mu(2)-Br)(2)Cu units of the butterfly-type with short Cu center dot center dot center dot Cu separations of 2.679(1) and 2.613(1) angstrom. In contrast to the common planar rhomboid Cu(mu(2)-Br)(2)Cu cluster, this butterfly-shaped geometry of the core …
Regio- and Stereoselective Synthesis of Spiropyrrolizidines and Piperazines through Azomethine Ylide Cycloaddition Reaction.
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…
ChemInform Abstract: Regio- and Stereoselective Synthesis of Spiropyrrolizidines and Piperazines Through Azomethine Ylide Cycloaddition Reaction.
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…
CCDC 1029334: Experimental Crystal Structure Determination
Related Article: Chourouk Mhiri, Fadwa Rouatbi, Sarra Boudriga, Moheddine Askri, Kabula Ciamala, Michael Knorr, Karin Monnier-Jobé, Abderrahim Khatyr, Yoann Rousselin, Marek M. Kubicki|2015|Mediterranean J.Chem.|4|30|doi:10.13171/mjc.4.1.2015.18.02.09.52/askri
CCDC 1029336: Experimental Crystal Structure Determination
Related Article: Chourouk Mhiri, Fadwa Rouatbi, Sarra Boudriga, Moheddine Askri, Kabula Ciamala, Michael Knorr, Karin Monnier-Jobé, Abderrahim Khatyr, Yoann Rousselin, Marek M. Kubicki|2015|Mediterranean J.Chem.|4|30|doi:10.13171/mjc.4.1.2015.18.02.09.52/askri
CCDC 1405446: Experimental Crystal Structure Determination
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
CCDC 1405448: Experimental Crystal Structure Determination
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
CCDC 1405449: Experimental Crystal Structure Determination
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
CCDC 1479591: Experimental Crystal Structure Determination
Related Article: Marwa Chaabéne, Abderrahim Khatyr, Michael Knorr, Moheddine Askri, Yoann Rousselin, Marek M. Kubicki|2016|Inorg.Chim.Acta|451|177|doi:10.1016/j.ica.2016.07.023
CCDC 1405447: Experimental Crystal Structure Determination
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
CCDC 1479590: Experimental Crystal Structure Determination
Related Article: Marwa Chaabéne, Abderrahim Khatyr, Michael Knorr, Moheddine Askri, Yoann Rousselin, Marek M. Kubicki|2016|Inorg.Chim.Acta|451|177|doi:10.1016/j.ica.2016.07.023
CCDC 1479592: Experimental Crystal Structure Determination
Related Article: Marwa Chaabéne, Abderrahim Khatyr, Michael Knorr, Moheddine Askri, Yoann Rousselin, Marek M. Kubicki|2016|Inorg.Chim.Acta|451|177|doi:10.1016/j.ica.2016.07.023
CCDC 1447439: Experimental Crystal Structure Determination
Related Article: Fadwa Rouatbi, Chourouk Mhiri, Moheddine Askri, Michael Knorr, Yoann Rousselin and Marek M. Kubicki|2017|J.Heterocycl.Chem.|54|1152|doi:10.1002/jhet.2684
CCDC 1447438: Experimental Crystal Structure Determination
Related Article: Fadwa Rouatbi, Chourouk Mhiri, Moheddine Askri, Michael Knorr, Yoann Rousselin and Marek M. Kubicki|2017|J.Heterocycl.Chem.|54|1152|doi:10.1002/jhet.2684
CCDC 1029335: Experimental Crystal Structure Determination
Related Article: Chourouk Mhiri, Fadwa Rouatbi, Sarra Boudriga, Moheddine Askri, Kabula Ciamala, Michael Knorr, Karin Monnier-Jobé, Abderrahim Khatyr, Yoann Rousselin, Marek M. Kubicki|2015|Mediterranean J.Chem.|4|30|doi:10.13171/mjc.4.1.2015.18.02.09.52/askri