A Direct and an Efficient Regioselective Synthesis of 1,2-Benzothiazine 1,1-dioxides, β-Carbolinones, Indolo[2,3-<i>c</i>]pyran-1-ones, Indolo[3,2-<i>c</i>]pyran-1-ones, Thieno[2,3-<i>c</i>]pyran-7-ones and Pyrano[3’,4’:4,5]imidazo[1,2-<i>a</i>]pyridin-1-ones via Tandem Stille/Heterocyclization Reaction
A general regioselective one-pot synthesis of 1,2-benzothiazine 1,1-dioxides from 2-iodo benzenesulfonamide moieties and allenylstannanes is described using a domino Stille-like/Azacyclization reaction. The conditions developed also opened a novel access to β-carbolinones, indolopyranones, thienopyr...
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| Format: | Article |
| Language: | English |
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MDPI AG
2020-11-01
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| Series: | Molecules |
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| Online Access: | https://www.mdpi.com/1420-3049/25/21/5137 |
| _version_ | 1797548822866427904 |
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| author | Badr Jismy Khalil Cherry Carine Maaliki Samuel Inack Ngi Mohamed Abarbri |
| author_facet | Badr Jismy Khalil Cherry Carine Maaliki Samuel Inack Ngi Mohamed Abarbri |
| author_sort | Badr Jismy |
| collection | DOAJ |
| description | A general regioselective one-pot synthesis of 1,2-benzothiazine 1,1-dioxides from 2-iodo benzenesulfonamide moieties and allenylstannanes is described using a domino Stille-like/Azacyclization reaction. The conditions developed also opened a novel access to β-carbolinones, indolopyranones, thienopyranones and pyrano-imidazopyridines. |
| first_indexed | 2024-03-10T15:05:14Z |
| format | Article |
| id | doaj.art-8fd901e66b38454fbf934a47afdd53e2 |
| institution | Directory Open Access Journal |
| issn | 1420-3049 |
| language | English |
| last_indexed | 2024-03-10T15:05:14Z |
| publishDate | 2020-11-01 |
| publisher | MDPI AG |
| record_format | Article |
| series | Molecules |
| spelling | doaj.art-8fd901e66b38454fbf934a47afdd53e22023-11-20T19:48:19ZengMDPI AGMolecules1420-30492020-11-012521513710.3390/molecules25215137A Direct and an Efficient Regioselective Synthesis of 1,2-Benzothiazine 1,1-dioxides, β-Carbolinones, Indolo[2,3-<i>c</i>]pyran-1-ones, Indolo[3,2-<i>c</i>]pyran-1-ones, Thieno[2,3-<i>c</i>]pyran-7-ones and Pyrano[3’,4’:4,5]imidazo[1,2-<i>a</i>]pyridin-1-ones via Tandem Stille/Heterocyclization ReactionBadr Jismy0Khalil Cherry1Carine Maaliki2Samuel Inack Ngi3Mohamed Abarbri4Laboratoire de Physico-Chimie des Matériaux et des Electrolytes Pour l’Energie (PCM2E), EA 6299, Avenue Monge, Faculté des Sciences, Université de Tours, Parc de Grandmont, 37200 Tours, FranceLaboratoire Matériaux, Catalyse, Environnement et Méthodes Analytiques (MCEMA), Campus Universitaire de Hadat, Université Libanaise, Beyrouth, LebanonLaboratoire de Physico-Chimie des Matériaux et des Electrolytes Pour l’Energie (PCM2E), EA 6299, Avenue Monge, Faculté des Sciences, Université de Tours, Parc de Grandmont, 37200 Tours, FranceIKAMBA Organics, rue Edouard Branly, 37230 Fondettes, FranceLaboratoire de Physico-Chimie des Matériaux et des Electrolytes Pour l’Energie (PCM2E), EA 6299, Avenue Monge, Faculté des Sciences, Université de Tours, Parc de Grandmont, 37200 Tours, FranceA general regioselective one-pot synthesis of 1,2-benzothiazine 1,1-dioxides from 2-iodo benzenesulfonamide moieties and allenylstannanes is described using a domino Stille-like/Azacyclization reaction. The conditions developed also opened a novel access to β-carbolinones, indolopyranones, thienopyranones and pyrano-imidazopyridines.https://www.mdpi.com/1420-3049/25/21/5137regioselective synthesis1,2-benzothiazine 1,1-dioxidesβ-carbolinonesindolo[2,3-<i>c</i>] and [3,2-<i>c</i>]pyrane-1-one derivativesStille/Heterocyclization reaction |
| spellingShingle | Badr Jismy Khalil Cherry Carine Maaliki Samuel Inack Ngi Mohamed Abarbri A Direct and an Efficient Regioselective Synthesis of 1,2-Benzothiazine 1,1-dioxides, β-Carbolinones, Indolo[2,3-<i>c</i>]pyran-1-ones, Indolo[3,2-<i>c</i>]pyran-1-ones, Thieno[2,3-<i>c</i>]pyran-7-ones and Pyrano[3’,4’:4,5]imidazo[1,2-<i>a</i>]pyridin-1-ones via Tandem Stille/Heterocyclization Reaction Molecules regioselective synthesis 1,2-benzothiazine 1,1-dioxides β-carbolinones indolo[2,3-<i>c</i>] and [3,2-<i>c</i>]pyrane-1-one derivatives Stille/Heterocyclization reaction |
| title | A Direct and an Efficient Regioselective Synthesis of 1,2-Benzothiazine 1,1-dioxides, β-Carbolinones, Indolo[2,3-<i>c</i>]pyran-1-ones, Indolo[3,2-<i>c</i>]pyran-1-ones, Thieno[2,3-<i>c</i>]pyran-7-ones and Pyrano[3’,4’:4,5]imidazo[1,2-<i>a</i>]pyridin-1-ones via Tandem Stille/Heterocyclization Reaction |
| title_full | A Direct and an Efficient Regioselective Synthesis of 1,2-Benzothiazine 1,1-dioxides, β-Carbolinones, Indolo[2,3-<i>c</i>]pyran-1-ones, Indolo[3,2-<i>c</i>]pyran-1-ones, Thieno[2,3-<i>c</i>]pyran-7-ones and Pyrano[3’,4’:4,5]imidazo[1,2-<i>a</i>]pyridin-1-ones via Tandem Stille/Heterocyclization Reaction |
| title_fullStr | A Direct and an Efficient Regioselective Synthesis of 1,2-Benzothiazine 1,1-dioxides, β-Carbolinones, Indolo[2,3-<i>c</i>]pyran-1-ones, Indolo[3,2-<i>c</i>]pyran-1-ones, Thieno[2,3-<i>c</i>]pyran-7-ones and Pyrano[3’,4’:4,5]imidazo[1,2-<i>a</i>]pyridin-1-ones via Tandem Stille/Heterocyclization Reaction |
| title_full_unstemmed | A Direct and an Efficient Regioselective Synthesis of 1,2-Benzothiazine 1,1-dioxides, β-Carbolinones, Indolo[2,3-<i>c</i>]pyran-1-ones, Indolo[3,2-<i>c</i>]pyran-1-ones, Thieno[2,3-<i>c</i>]pyran-7-ones and Pyrano[3’,4’:4,5]imidazo[1,2-<i>a</i>]pyridin-1-ones via Tandem Stille/Heterocyclization Reaction |
| title_short | A Direct and an Efficient Regioselective Synthesis of 1,2-Benzothiazine 1,1-dioxides, β-Carbolinones, Indolo[2,3-<i>c</i>]pyran-1-ones, Indolo[3,2-<i>c</i>]pyran-1-ones, Thieno[2,3-<i>c</i>]pyran-7-ones and Pyrano[3’,4’:4,5]imidazo[1,2-<i>a</i>]pyridin-1-ones via Tandem Stille/Heterocyclization Reaction |
| title_sort | direct and an efficient regioselective synthesis of 1 2 benzothiazine 1 1 dioxides β carbolinones indolo 2 3 i c i pyran 1 ones indolo 3 2 i c i pyran 1 ones thieno 2 3 i c i pyran 7 ones and pyrano 3 4 4 5 imidazo 1 2 i a i pyridin 1 ones via tandem stille heterocyclization reaction |
| topic | regioselective synthesis 1,2-benzothiazine 1,1-dioxides β-carbolinones indolo[2,3-<i>c</i>] and [3,2-<i>c</i>]pyrane-1-one derivatives Stille/Heterocyclization reaction |
| url | https://www.mdpi.com/1420-3049/25/21/5137 |
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