Gold-catalyzed bicyclic annulations between 4-hydroxy-1,5-diynamides and nitrones for the synthesis of cyclopentene-fused isoxazole carboxamides

Chandrima Maitra; Ting-Yi Chuang; Tzuhsiung Yang; Rai-Shung Liu

doi:10.1039/d5cc00353a

Gold-catalyzed bicyclic annulations between 4-hydroxy-1,5-diynamides and nitrones for the synthesis of cyclopentene-fused isoxazole carboxamides

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Gold-catalyzed bicyclic annulations between 4-hydroxy-1,5-diynamides and nitrones for the synthesis of cyclopentene-fused isoxazole carboxamides

Chandrima Maitra, Ting-Yi Chuang, Tzuhsiung Yang 和 Rai-Shung Liu

Chemical communications (Cambridge, England), 卷.61(49), 頁碼.8931-8934

12/06/2025

DOI: https://doi.org/10.1039/d5cc00353a

PMID: 40396248

Web of Science ID: WOS:001491704100001

摘要

This work reports gold-catalyzed reactions between 4-hydroxy-1,5-diynamides and nitrones, demonstrating the success of using 1, -diynes to achieve bicyclic annulations. Mechanistic studies show the importance of the hydroxyl group to form reactive intermediates, followed by a [3+2]-nitrone cycloaddition with alkenylgold intermediates. This mechanism is supported by DFT-calculations.

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題名: Gold-catalyzed bicyclic annulations between 4-hydroxy-1,5-diynamides and nitrones for the synthesis of cyclopentene-fused isoxazole carboxamides
創作者：: Chandrima Maitra - National Tsing Hua University
Ting-Yi Chuang - National Tsing Hua University
Tzuhsiung Yang - National Tsing Hua University
Rai-Shung Liu - National Tsing Hua University
出版者: ROYAL SOC CHEMISTRY
總頁數: 4
補助款備註: National Science and Technology Council, Taiwan: NSTC 113-2113-M-007-014, NSTC 111-2113-M-007-031-MY3 Yushan Young Scholar Program, under the Ministry of Education (MOE), Taiwan: MOE-111-YSFMS-0002-002-P1
We thank the National Science and Technology Council(NSTC 113-2113-M-007-014 and NSTC 111-2113-M-007-031-MY3), Taiwan, for their financial support of this work. Wethank the National Center for High-performance Computing(NCHC) for providing computational and storage resources. In addition, we thank the support from the Yushan Young Scholar Program, under the Ministry of Education (MOE), Taiwan(MOE-111-YSFMS-0002-002-P1)
學術資源類型: 期刊文章
出版日期: 12/06/2025
出版資訊: Chemical communications (Cambridge, England), 卷.61(49), 頁碼.8931-8934
語言: 英語

Gold-catalyzed bicyclic annulations between 4-hydroxy-1,5-diynamides and nitrones for the synthesis of cyclopentene-fused isoxazole carboxamides

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