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*

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

1 Citation (Scopus)

Abstract

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.).

Original languageEnglish
Pages (from-to)1391-1397
Number of pages7
JournalAdvanced Synthesis and Catalysis
Volume365
Issue number9
DOIs
Publication statusPublished - 2023 May 12

Keywords

  • cycloaddition
  • molecular diversity
  • nitrogen heterocycles
  • rearrangement
  • regioselectivity

ASJC Scopus subject areas

  • Catalysis
  • Organic Chemistry

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