Synthesis of functionalized tetrahydro-dispiro[pyrazolone 4, 2′-pyran-5′, 4″-pyrazolone] scaffolds via an Oxa-Michael-initiated cascade [4 + 2] annulation reaction using pyrazoledione-derived MBH-alcohols
In this study, an efficient protocol was developed for synthesizing tetrahydro-dispiro[pyrazolone 4, 2′-pyran-5′, 4″-pyrazolone] scaffolds, using pyrazoledione-derived MBH alcohols and arylidene pyrazolones. The reaction proceeds through an oxa-Michael-initiated cascade [4 + 2] annulation under meta...
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| Main Authors: | , , , , , , |
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| Format: | Article |
| Language: | English |
| Published: |
Elsevier
2025-09-01
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| Series: | Results in Chemistry |
| Subjects: | |
| Online Access: | http://www.sciencedirect.com/science/article/pii/S2211715625005879 |
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| Summary: | In this study, an efficient protocol was developed for synthesizing tetrahydro-dispiro[pyrazolone 4, 2′-pyran-5′, 4″-pyrazolone] scaffolds, using pyrazoledione-derived MBH alcohols and arylidene pyrazolones. The reaction proceeds through an oxa-Michael-initiated cascade [4 + 2] annulation under metal-free conditions, affording a range of novel tetrahydrodispiro[pyrazolone-pyran-pyrazolone] derivatives with yields between 50 and 89 % and diastereoselectivities from 2.5:1 to >20:1. As a novel oxa-Michael donors, pyrazoledione-derived MBH alcohols were employed for the first time as a key substrate in this annulation reaction. |
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| ISSN: | 2211-7156 |