0000000001299879
AUTHOR
Sarra Boudriga
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…
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 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 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