Acid-Catalyzed, Metal- and Oxidant-Free C=C Bond Cleavage of Enaminones: One-Pot Synthesis of 3,4-Dihydroquinazolines
In this study, we present the HOAc-catalyzed selective cleavage of the C=C double bond of enaminones, enabling the formation of a new C–N bond and a new C=N bond for the one-pot synthesis of 2-substituted 3,4-dihydroquinazolines directly from ynones and 2-(aminomethyl)anilines. This method operates...
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MDPI AG
2025-01-01
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| Series: | Molecules |
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| Online Access: | https://www.mdpi.com/1420-3049/30/2/350 |
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| author | Ting Chen Ting Huang Moudan Ye Jinhai Shen |
| author_facet | Ting Chen Ting Huang Moudan Ye Jinhai Shen |
| author_sort | Ting Chen |
| collection | DOAJ |
| description | In this study, we present the HOAc-catalyzed selective cleavage of the C=C double bond of enaminones, enabling the formation of a new C–N bond and a new C=N bond for the one-pot synthesis of 2-substituted 3,4-dihydroquinazolines directly from ynones and 2-(aminomethyl)anilines. This method operates in ethanol under transition-metal-free and oxidant-free conditions, offering a sustainable and efficient approach for the synthesis of 3,4-dihydroquinazolines with broad functional group tolerance. |
| format | Article |
| id | doaj-art-f1e35ebf0d414cecb384052a2650a00a |
| institution | Kabale University |
| issn | 1420-3049 |
| language | English |
| publishDate | 2025-01-01 |
| publisher | MDPI AG |
| record_format | Article |
| series | Molecules |
| spelling | doaj-art-f1e35ebf0d414cecb384052a2650a00a2025-01-24T13:43:43ZengMDPI AGMolecules1420-30492025-01-0130235010.3390/molecules30020350Acid-Catalyzed, Metal- and Oxidant-Free C=C Bond Cleavage of Enaminones: One-Pot Synthesis of 3,4-DihydroquinazolinesTing Chen0Ting Huang1Moudan Ye2Jinhai Shen3School of Environment and Public Health, Xiamen Huaxia University, Xiamen 361024, ChinaSchool of Environment and Public Health, Xiamen Huaxia University, Xiamen 361024, ChinaSchool of Environment and Public Health, Xiamen Huaxia University, Xiamen 361024, ChinaSchool of Environment and Public Health, Xiamen Huaxia University, Xiamen 361024, ChinaIn this study, we present the HOAc-catalyzed selective cleavage of the C=C double bond of enaminones, enabling the formation of a new C–N bond and a new C=N bond for the one-pot synthesis of 2-substituted 3,4-dihydroquinazolines directly from ynones and 2-(aminomethyl)anilines. This method operates in ethanol under transition-metal-free and oxidant-free conditions, offering a sustainable and efficient approach for the synthesis of 3,4-dihydroquinazolines with broad functional group tolerance.https://www.mdpi.com/1420-3049/30/2/3503,4-dihydroquinazolineenaminonesC–C bond cleavageynonesorganic synthesis |
| spellingShingle | Ting Chen Ting Huang Moudan Ye Jinhai Shen Acid-Catalyzed, Metal- and Oxidant-Free C=C Bond Cleavage of Enaminones: One-Pot Synthesis of 3,4-Dihydroquinazolines Molecules 3,4-dihydroquinazoline enaminones C–C bond cleavage ynones organic synthesis |
| title | Acid-Catalyzed, Metal- and Oxidant-Free C=C Bond Cleavage of Enaminones: One-Pot Synthesis of 3,4-Dihydroquinazolines |
| title_full | Acid-Catalyzed, Metal- and Oxidant-Free C=C Bond Cleavage of Enaminones: One-Pot Synthesis of 3,4-Dihydroquinazolines |
| title_fullStr | Acid-Catalyzed, Metal- and Oxidant-Free C=C Bond Cleavage of Enaminones: One-Pot Synthesis of 3,4-Dihydroquinazolines |
| title_full_unstemmed | Acid-Catalyzed, Metal- and Oxidant-Free C=C Bond Cleavage of Enaminones: One-Pot Synthesis of 3,4-Dihydroquinazolines |
| title_short | Acid-Catalyzed, Metal- and Oxidant-Free C=C Bond Cleavage of Enaminones: One-Pot Synthesis of 3,4-Dihydroquinazolines |
| title_sort | acid catalyzed metal and oxidant free c c bond cleavage of enaminones one pot synthesis of 3 4 dihydroquinazolines |
| topic | 3,4-dihydroquinazoline enaminones C–C bond cleavage ynones organic synthesis |
| url | https://www.mdpi.com/1420-3049/30/2/350 |
| work_keys_str_mv | AT tingchen acidcatalyzedmetalandoxidantfreeccbondcleavageofenaminonesonepotsynthesisof34dihydroquinazolines AT tinghuang acidcatalyzedmetalandoxidantfreeccbondcleavageofenaminonesonepotsynthesisof34dihydroquinazolines AT moudanye acidcatalyzedmetalandoxidantfreeccbondcleavageofenaminonesonepotsynthesisof34dihydroquinazolines AT jinhaishen acidcatalyzedmetalandoxidantfreeccbondcleavageofenaminonesonepotsynthesisof34dihydroquinazolines |