0000000001299881
AUTHOR
Kabula Ciamala
Synthesis of Isoxazole and 1,2,3-Triazole Isoindole Derivatives via Silver- and Copper-Catalyzed 1,3-Dipolar Cycloaddition Reaction.
International audience; The CuI-or Ag 2 CO 3-catalyzed [3+2] cycloaddition of propargyl-substituted dihydroisoindolin-1-one (3) with arylnitrile oxides 1a-d (Ar = Ph, p-MeC 6 H 4 , p-MeOC 6 H 4 , p-ClC 6 H 4) produces in good yields novel 3,5-disubstituted isoxazoles 4 of the ethyl-2-benzyl-3-oxo-1-((3-arylisoxazol-5yl)methyl)-2,3-dihydro-1H-isoindole-1-carboxylate type. With aryl azides 2a-d (Ar = Ph, p-MeC 6 H 4 , p-OMeC 6 H 4 , p-ClC 6 H 4), a series of 1,4-disubstituted 1,2,3-triazoles 6 (ethyl-2-benzyl-3-oxo-1-((1-aryl-1H-1,2,3-triazol-4-yl)methyl)-2,3-dihydro-1H-isoindole-1-carboxylates) was obtained. The reactions proceed in a regioselective manner affording exclusively racemic adduc…
1,3-Dipolar cycloaddition of diaryldiazomethanes across N-ethoxy-carbonyl-N-(2,2,2-trichloroethylidene)amine and reactivity of the resulting 2-azabutadienes towards thiolates and cyclic amides
Abstract 1,3-dipolar cycloaddition of diaryldiazomethanes Ar2C N2 across Cl3C–CH N–CO2Et 1 yields Δ3-1,2,4-triazolines 2. Thermolysis of 2 leads, via transient azomethine ylides 3, to diaryldichloroazabutadienes [Ar(Ar')C N–CH CCl2] 4. Treatment of 4a (Ar = Ar' = C6H5) and 4c (Ar = Ar' = p-ClC6H4) with NaSR in DMF yields 2-azabutadienes [Ar2C N–C(H) C(SR)2] 5. In contrast, nucleophilic attack of NaStBu on 4 affords azadienic dithioethers [Ar2C N–C(StBu) C(H)(StBu)] (7a Ar = C6H5; 7b Ar' = p-ClC6H4). The reaction of 4a with NaSEt conducted in neat EtSH produces [Ph2C N–C(H)(SEt)–CCl2H] 8, which after dehydrochloration by NaOMe and subsequent addition of NaSEt is converted to [Ph2C N–C(SEt) C…
1,3-Dipolar Cycloaddition Reactions of Indan-1-one Enamines across Arylnitrile Oxides Leading to Novel Cyclic Isoxazoline Derivatives
Synthesis of a series of cyclic fused-isoxazolines has been accomplished by regioselective and diastereoselective 1,3-dipolar cycloaddition of 3-methylindan-1-one enamines (1a, 1b, 1c) and 3-phenylindan-1-one enamines (2a, 2b, 2c) to arylnitrile oxides (3d, 3e, 3f, 3g, 3h). The structure of the cycloadducts was elucidated by 1H and 13C NMR spectroscopy. The proposed regio- and stereochemistry of fused-compounds (4) and (5) has also been corroborated by two single-crystal X-ray diffraction studies carried out on 4-methyl-8b-morpholinyl-3-(p-tolyl)-4H-3a,8b-dihydroindeno[2,3-d]isoxazoline (4be) and 3-(p-anisyl)-4-phenyl-8b-pyrrolidinyl-4H-3a,8b-dihydroindeno[2,3-d]isoxazoline (5af) and by mea…
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 835277: Experimental Crystal Structure Determination
Related Article: Rodolphe Kinghat, Gérard Schmitt, Kabula Ciamala, Abderrahim Khatyr, Michael Knorr, Sandrine Jacquot-Rousseau, Yoann Rousselin, Marek M. Kubicki|2016|Comptes Rendus Chimie|19|320|doi:10.1016/j.crci.2015.09.017
CCDC 835276: Experimental Crystal Structure Determination
Related Article: Rodolphe Kinghat, Gérard Schmitt, Kabula Ciamala, Abderrahim Khatyr, Michael Knorr, Sandrine Jacquot-Rousseau, Yoann Rousselin, Marek M. Kubicki|2016|Comptes Rendus Chimie|19|320|doi:10.1016/j.crci.2015.09.017
CCDC 830704: Experimental Crystal Structure Determination
Related Article: Hanene Jelizi, Nadia Wannassi, Mohamed El Baker Rammah, Kabula Ciamala, Michael Knorr, Yoann Rousselin, Marek M. Kubicki, Carsten Strohmann and Mironel Enescu|2014|J.Heterocycl.Chem.|51|383|doi:10.1002/jhet.1588
CCDC 831070: Experimental Crystal Structure Determination
Related Article: Hanene Jelizi, Nadia Wannassi, Mohamed El Baker Rammah, Kabula Ciamala, Michael Knorr, Yoann Rousselin, Marek M. Kubicki, Carsten Strohmann and Mironel Enescu|2014|J.Heterocycl.Chem.|51|383|doi:10.1002/jhet.1588
CCDC 889646: Experimental Crystal Structure Determination
Related Article: Rodolphe Kinghat, Gérard Schmitt, Kabula Ciamala, Abderrahim Khatyr, Michael Knorr, Sandrine Jacquot-Rousseau, Yoann Rousselin, Marek M. Kubicki|2016|Comptes Rendus Chimie|19|320|doi:10.1016/j.crci.2015.09.017
CCDC 941426: Experimental Crystal Structure Determination
Related Article: Rodolphe Kinghat, Gérard Schmitt, Kabula Ciamala, Abderrahim Khatyr, Michael Knorr, Sandrine Jacquot-Rousseau, Yoann Rousselin, Marek M. Kubicki|2016|Comptes Rendus Chimie|19|320|doi:10.1016/j.crci.2015.09.017
CCDC 1405500: Experimental Crystal Structure Determination
Related Article: Mohamed Mehdi Rammah, Wafa Gati, Hasan Mtiraoui, Mohamed El Baker Rammah, Kabula Ciamala, Michael Knorr, Yoann Rousselin, Marek M. Kubicki|2016|Molecules|21|307|doi:10.3390/molecules21030307
CCDC 835275: Experimental Crystal Structure Determination
Related Article: Rodolphe Kinghat, Gérard Schmitt, Kabula Ciamala, Abderrahim Khatyr, Michael Knorr, Sandrine Jacquot-Rousseau, Yoann Rousselin, Marek M. Kubicki|2016|Comptes Rendus Chimie|19|320|doi:10.1016/j.crci.2015.09.017
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