Cascade Reactions of Indigo with an Allenylic Reactant
The base-enabled reaction of buta-2,3-dien-1-yl methanesulfonate with the readily available and cheap dye indigo resulted in the convenient one-pot synthesis of benzoindolonaphthyridinedione and benzoazepinopyridoindolediones, with the latter representing two novel heterocyclic scaffolds. Despite th...
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| Format: | Article |
| Language: | English |
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MDPI AG
2025-07-01
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| Series: | Molecules |
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| Online Access: | https://www.mdpi.com/1420-3049/30/14/2899 |
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| _version_ | 1849732785445535744 |
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| author | Dyah U. C. Rahayu Christopher Richardson John B. Bremner Paul A. Keller |
| author_facet | Dyah U. C. Rahayu Christopher Richardson John B. Bremner Paul A. Keller |
| author_sort | Dyah U. C. Rahayu |
| collection | DOAJ |
| description | The base-enabled reaction of buta-2,3-dien-1-yl methanesulfonate with the readily available and cheap dye indigo resulted in the convenient one-pot synthesis of benzoindolonaphthyridinedione and benzoazepinopyridoindolediones, with the latter representing two novel heterocyclic scaffolds. Despite the low yields, the allenylic alkylation of indigo significantly contributes to the new chemistry of this compound, providing new mechanistic insights and reactivity boundaries. |
| format | Article |
| id | doaj-art-aeef77e314e843669b260319985bc155 |
| institution | DOAJ |
| issn | 1420-3049 |
| language | English |
| publishDate | 2025-07-01 |
| publisher | MDPI AG |
| record_format | Article |
| series | Molecules |
| spelling | doaj-art-aeef77e314e843669b260319985bc1552025-08-20T03:08:13ZengMDPI AGMolecules1420-30492025-07-013014289910.3390/molecules30142899Cascade Reactions of Indigo with an Allenylic ReactantDyah U. C. Rahayu0Christopher Richardson1John B. Bremner2Paul A. Keller3School of Science, Molecular Horizons, University of Wollongong, Wollongong, NSW 2522, AustraliaSchool of Science, Molecular Horizons, University of Wollongong, Wollongong, NSW 2522, AustraliaSchool of Science, Molecular Horizons, University of Wollongong, Wollongong, NSW 2522, AustraliaSchool of Science, Molecular Horizons, University of Wollongong, Wollongong, NSW 2522, AustraliaThe base-enabled reaction of buta-2,3-dien-1-yl methanesulfonate with the readily available and cheap dye indigo resulted in the convenient one-pot synthesis of benzoindolonaphthyridinedione and benzoazepinopyridoindolediones, with the latter representing two novel heterocyclic scaffolds. Despite the low yields, the allenylic alkylation of indigo significantly contributes to the new chemistry of this compound, providing new mechanistic insights and reactivity boundaries.https://www.mdpi.com/1420-3049/30/14/2899indigocascade reactionallenylic electrophilebenzoindolonaphthyridinedionebenzoazepinopyridoindolediones |
| spellingShingle | Dyah U. C. Rahayu Christopher Richardson John B. Bremner Paul A. Keller Cascade Reactions of Indigo with an Allenylic Reactant Molecules indigo cascade reaction allenylic electrophile benzoindolonaphthyridinedione benzoazepinopyridoindolediones |
| title | Cascade Reactions of Indigo with an Allenylic Reactant |
| title_full | Cascade Reactions of Indigo with an Allenylic Reactant |
| title_fullStr | Cascade Reactions of Indigo with an Allenylic Reactant |
| title_full_unstemmed | Cascade Reactions of Indigo with an Allenylic Reactant |
| title_short | Cascade Reactions of Indigo with an Allenylic Reactant |
| title_sort | cascade reactions of indigo with an allenylic reactant |
| topic | indigo cascade reaction allenylic electrophile benzoindolonaphthyridinedione benzoazepinopyridoindolediones |
| url | https://www.mdpi.com/1420-3049/30/14/2899 |
| work_keys_str_mv | AT dyahucrahayu cascadereactionsofindigowithanallenylicreactant AT christopherrichardson cascadereactionsofindigowithanallenylicreactant AT johnbbremner cascadereactionsofindigowithanallenylicreactant AT paulakeller cascadereactionsofindigowithanallenylicreactant |