Diversity-Oriented Synthesis of Spiro- and 3-Methylene-hydroquinoline-Indandiones via an Organobase-Controlled Cascade Strategy

Tsai Hui Lung, Yi Ru Chen, Chen Ling Chang, Wey Chyng Jeng, Pei Shan Wu, Sandip Sambhaji Vagh, Gangababu Marri, Yi Fang Lin, Wenwei Lin*

*此作品的通信作者

研究成果: 雜誌貢獻期刊論文同行評審

2 引文 斯高帕斯(Scopus)

摘要

The catalyst-controlled diversity-oriented synthesis of spirohydroquinoline-indandiones and 3-methylenehydroquinoline-indandiones from ortho-sulfonamidophenyl-substituted para-quinone methides and allylidene-indandiones is reported. The strategies utilized an organobase such as DMAP or TMG to control the reaction pathway chemoselectively, furnishing the corresponding products in 40–99% yields with excellent diastereoselectivities. The mechanistic studies revealed that spirohydroquinoline-indandione was the kinetic product to afford 3-methylenehydroquinoline-indandione in the presence of TMG, which probably involved an unusual base-initiated 1,3-nitrogen rearrangement process. (Figure presented.).

原文英語
頁(從 - 到)1391-1397
頁數7
期刊Advanced Synthesis and Catalysis
365
發行號9
DOIs
出版狀態已發佈 - 2023 5月 12

ASJC Scopus subject areas

  • 催化
  • 有機化學

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