On the regioselective molecular sieves-promoted oxidative three-component synthesis of fused-benzimidazoles from $\beta $-ketoesters
The regioselectivity of molecular sieves-promoted oxidative three-component reaction between $\beta $-ketoesters, aromatic o-diamines and acrolein, leading to pyrido[1,2-a]benzimidazoles, has been investigated by a combination of experimental and theoretical studies. Molecular sieves act both as het...
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Académie des sciences
2022-02-01
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| Series: | Comptes Rendus. Chimie |
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| Online Access: | https://comptes-rendus.academie-sciences.fr/chimie/articles/10.5802/crchim.137/ |
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| author | Martin, Anthony Cheshmedzhieva, Diana Palermo, Valeria Liéby-Muller, Frédéric Romanelli, Gustavo P. Gaudel-Siri, Anouk Coquerel, Yoann Constantieux, Thierry Rodriguez, Jean |
| author_facet | Martin, Anthony Cheshmedzhieva, Diana Palermo, Valeria Liéby-Muller, Frédéric Romanelli, Gustavo P. Gaudel-Siri, Anouk Coquerel, Yoann Constantieux, Thierry Rodriguez, Jean |
| author_sort | Martin, Anthony |
| collection | DOAJ |
| description | The regioselectivity of molecular sieves-promoted oxidative three-component reaction between $\beta $-ketoesters, aromatic o-diamines and acrolein, leading to pyrido[1,2-a]benzimidazoles, has been investigated by a combination of experimental and theoretical studies. Molecular sieves act both as heterogeneous catalyst and dehydrating agent and their role has been modeled in the theoretical approach. The modulation of the reactivity of the aromatic diamine partner as a function of the nature of the substituents of the aromatic ring and its influence on the regioselectivity of the reaction could be rationalized. |
| format | Article |
| id | doaj-art-694d422d00564994bd3791b3452f57f8 |
| institution | Kabale University |
| issn | 1878-1543 |
| language | English |
| publishDate | 2022-02-01 |
| publisher | Académie des sciences |
| record_format | Article |
| series | Comptes Rendus. Chimie |
| spelling | doaj-art-694d422d00564994bd3791b3452f57f82025-02-07T13:31:13ZengAcadémie des sciencesComptes Rendus. Chimie1878-15432022-02-0125G1192910.5802/crchim.13710.5802/crchim.137On the regioselective molecular sieves-promoted oxidative three-component synthesis of fused-benzimidazoles from $\beta $-ketoestersMartin, Anthony0Cheshmedzhieva, Diana1https://orcid.org/0000-0002-9344-9282Palermo, Valeria2https://orcid.org/0000-0003-2965-5265Liéby-Muller, Frédéric3Romanelli, Gustavo P.4https://orcid.org/0000-0002-3529-4753Gaudel-Siri, Anouk5https://orcid.org/0000-0003-4808-9588Coquerel, Yoann6https://orcid.org/0000-0003-0646-006XConstantieux, Thierry7https://orcid.org/0000-0002-8634-399XRodriguez, Jean8Aix-Marseille Univ, CNRS, Centrale Marseille, iSm2, Marseille, FranceFaculty of Chemistry and Pharmacy, University of Sofia, 1164 Sofia, BulgariaAix-Marseille Univ, CNRS, Centrale Marseille, iSm2, Marseille, France; Centro de Investigacion y Desarollo en Ciencias Aplicadas “Dr. Jorge J. Ronco”(CINDECACCT-CONICET) Universidad Nacional de La Plata, calle 47 N ∘ 257, B1900AJK La Plata, ArgentinaAix-Marseille Univ, CNRS, Centrale Marseille, iSm2, Marseille, France; Institut de Recherche Pierre Fabre 3, Av. Hubert Curien 31100 Toulouse, FranceCentro de Investigacion y Desarollo en Ciencias Aplicadas “Dr. Jorge J. Ronco”(CINDECACCT-CONICET) Universidad Nacional de La Plata, calle 47 N ∘ 257, B1900AJK La Plata, ArgentinaAix-Marseille Université, CNRS, ICR, Marseille, FranceAix-Marseille Univ, CNRS, Centrale Marseille, iSm2, Marseille, FranceAix-Marseille Univ, CNRS, Centrale Marseille, iSm2, Marseille, FranceAix-Marseille Univ, CNRS, Centrale Marseille, iSm2, Marseille, FranceThe regioselectivity of molecular sieves-promoted oxidative three-component reaction between $\beta $-ketoesters, aromatic o-diamines and acrolein, leading to pyrido[1,2-a]benzimidazoles, has been investigated by a combination of experimental and theoretical studies. Molecular sieves act both as heterogeneous catalyst and dehydrating agent and their role has been modeled in the theoretical approach. The modulation of the reactivity of the aromatic diamine partner as a function of the nature of the substituents of the aromatic ring and its influence on the regioselectivity of the reaction could be rationalized.https://comptes-rendus.academie-sciences.fr/chimie/articles/10.5802/crchim.137/Multicomponent reactionMichael additionBenzimidazoleMolecular sievesHeterocycles |
| spellingShingle | Martin, Anthony Cheshmedzhieva, Diana Palermo, Valeria Liéby-Muller, Frédéric Romanelli, Gustavo P. Gaudel-Siri, Anouk Coquerel, Yoann Constantieux, Thierry Rodriguez, Jean On the regioselective molecular sieves-promoted oxidative three-component synthesis of fused-benzimidazoles from $\beta $-ketoesters Comptes Rendus. Chimie Multicomponent reaction Michael addition Benzimidazole Molecular sieves Heterocycles |
| title | On the regioselective molecular sieves-promoted oxidative three-component synthesis of fused-benzimidazoles from $\beta $-ketoesters |
| title_full | On the regioselective molecular sieves-promoted oxidative three-component synthesis of fused-benzimidazoles from $\beta $-ketoesters |
| title_fullStr | On the regioselective molecular sieves-promoted oxidative three-component synthesis of fused-benzimidazoles from $\beta $-ketoesters |
| title_full_unstemmed | On the regioselective molecular sieves-promoted oxidative three-component synthesis of fused-benzimidazoles from $\beta $-ketoesters |
| title_short | On the regioselective molecular sieves-promoted oxidative three-component synthesis of fused-benzimidazoles from $\beta $-ketoesters |
| title_sort | on the regioselective molecular sieves promoted oxidative three component synthesis of fused benzimidazoles from beta ketoesters |
| topic | Multicomponent reaction Michael addition Benzimidazole Molecular sieves Heterocycles |
| url | https://comptes-rendus.academie-sciences.fr/chimie/articles/10.5802/crchim.137/ |
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