Acetic acid mediated Michael-addition/cyclization cascade sequence of cyclic diones and enones; A convenient, proficient, and eco-friendly access to the fused dihydropyrans
An acetic acid-mediated Michael addition-cyclization cascade sequence of cyclic diones and enones is developed to afford fused dihydropyrans. A broad range of structurally diverse aliphatic, aromatic, and functionalized enones are successfully employed under the optimized reaction conditions. The cu...
| Main Authors: | , , , , |
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| Format: | Article |
| Language: | English |
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Elsevier
2023-11-01
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| Series: | Journal of Saudi Chemical Society |
| Subjects: | |
| Online Access: | http://www.sciencedirect.com/science/article/pii/S1319610323001618 |
| _version_ | 1797378743453351936 |
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| author | Maira Hasnain Pasha Humaira Yasmeen Gondal Sami A. Alhussain Mavra Jamshaid Magdi E.A. Zaki |
| author_facet | Maira Hasnain Pasha Humaira Yasmeen Gondal Sami A. Alhussain Mavra Jamshaid Magdi E.A. Zaki |
| author_sort | Maira Hasnain Pasha |
| collection | DOAJ |
| description | An acetic acid-mediated Michael addition-cyclization cascade sequence of cyclic diones and enones is developed to afford fused dihydropyrans. A broad range of structurally diverse aliphatic, aromatic, and functionalized enones are successfully employed under the optimized reaction conditions. The current strategy takes advantage of using easily accessible and environmentally benign conditions to access the synthetically challenging 3,4-dihydropyran in high yields (up to 90%) and selectivity (up to 20:1). The applicability of these reaction conditions is underscored by successfully isolating the desired dihydropyrans from the Michael adduct, for the first time. Moreover, Density Functional Theory (DFT) provided a comprehensive analysis involving Frontier Molecular Orbital (FMO), Mulliken population, and Molecular Electrostatic Potential (MEP) investigations to gain deeper insights into the underlying reaction sequence. |
| first_indexed | 2024-03-08T20:12:07Z |
| format | Article |
| id | doaj.art-78844db6a93b45ce9417ceba9906e35d |
| institution | Directory Open Access Journal |
| issn | 1319-6103 |
| language | English |
| last_indexed | 2024-03-08T20:12:07Z |
| publishDate | 2023-11-01 |
| publisher | Elsevier |
| record_format | Article |
| series | Journal of Saudi Chemical Society |
| spelling | doaj.art-78844db6a93b45ce9417ceba9906e35d2023-12-23T05:20:12ZengElsevierJournal of Saudi Chemical Society1319-61032023-11-01276101757Acetic acid mediated Michael-addition/cyclization cascade sequence of cyclic diones and enones; A convenient, proficient, and eco-friendly access to the fused dihydropyransMaira Hasnain Pasha0Humaira Yasmeen Gondal1Sami A. Alhussain2Mavra Jamshaid3Magdi E.A. Zaki4Institute of Chemistry, University of Sargodha, Sargodha, PakistanInstitute of Chemistry, University of Sargodha, Sargodha, PakistanDepartment of Chemistry, College of Science, Imam Mohammad Ibn Saud Islamic University (IMSIU), Riyadh 13623, Saudi ArabiaInstitute of Chemistry, University of Sargodha, Sargodha, PakistanDepartment of Chemistry, College of Science, Imam Mohammad Ibn Saud Islamic University (IMSIU), Riyadh 13623, Saudi ArabiaAn acetic acid-mediated Michael addition-cyclization cascade sequence of cyclic diones and enones is developed to afford fused dihydropyrans. A broad range of structurally diverse aliphatic, aromatic, and functionalized enones are successfully employed under the optimized reaction conditions. The current strategy takes advantage of using easily accessible and environmentally benign conditions to access the synthetically challenging 3,4-dihydropyran in high yields (up to 90%) and selectivity (up to 20:1). The applicability of these reaction conditions is underscored by successfully isolating the desired dihydropyrans from the Michael adduct, for the first time. Moreover, Density Functional Theory (DFT) provided a comprehensive analysis involving Frontier Molecular Orbital (FMO), Mulliken population, and Molecular Electrostatic Potential (MEP) investigations to gain deeper insights into the underlying reaction sequence.http://www.sciencedirect.com/science/article/pii/S1319610323001618Cascade reactionsMichael addition-cyclizationDihydropyransCyclic enonesAcetic acid-mediated reactionsDFT studies |
| spellingShingle | Maira Hasnain Pasha Humaira Yasmeen Gondal Sami A. Alhussain Mavra Jamshaid Magdi E.A. Zaki Acetic acid mediated Michael-addition/cyclization cascade sequence of cyclic diones and enones; A convenient, proficient, and eco-friendly access to the fused dihydropyrans Journal of Saudi Chemical Society Cascade reactions Michael addition-cyclization Dihydropyrans Cyclic enones Acetic acid-mediated reactions DFT studies |
| title | Acetic acid mediated Michael-addition/cyclization cascade sequence of cyclic diones and enones; A convenient, proficient, and eco-friendly access to the fused dihydropyrans |
| title_full | Acetic acid mediated Michael-addition/cyclization cascade sequence of cyclic diones and enones; A convenient, proficient, and eco-friendly access to the fused dihydropyrans |
| title_fullStr | Acetic acid mediated Michael-addition/cyclization cascade sequence of cyclic diones and enones; A convenient, proficient, and eco-friendly access to the fused dihydropyrans |
| title_full_unstemmed | Acetic acid mediated Michael-addition/cyclization cascade sequence of cyclic diones and enones; A convenient, proficient, and eco-friendly access to the fused dihydropyrans |
| title_short | Acetic acid mediated Michael-addition/cyclization cascade sequence of cyclic diones and enones; A convenient, proficient, and eco-friendly access to the fused dihydropyrans |
| title_sort | acetic acid mediated michael addition cyclization cascade sequence of cyclic diones and enones a convenient proficient and eco friendly access to the fused dihydropyrans |
| topic | Cascade reactions Michael addition-cyclization Dihydropyrans Cyclic enones Acetic acid-mediated reactions DFT studies |
| url | http://www.sciencedirect.com/science/article/pii/S1319610323001618 |
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