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
Year: 2025
Type: article
Abstract: 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.
Source: Results in Chemistry
Authors: Xiaoming Zhou, Juan Du, JiPeng Yuan, Xuehan Wang, Hongli Yang, Xuekun Wang, Zhenzhen Gao
Institutions: Liaocheng University, Liaocheng People's Hospital
Language: English
Subfield: Organic Chemistry
Field: Chemistry
Domain: Physical Sciences
Open Access status: gold
Estimated APC paid: $1,870
Funders: National Natural Science Foundation of China, Liaocheng University, Natural Science Foundation of Shandong Province, Youth Innovation Technology Project of Higher School in Shandong Province, Science and Technology Support Plan for Youth Innovation of Colleges and Universities of Shandong Province of China
Awards: G1404186481, G288180848, G7317781158
OpenAlex ID: W4413231620