0000000000591327
AUTHOR
Saoussen Haddad
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 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