DBU-Catalyzed Inter- and Intramolecular Double Michael Addition of Donor–Acceptor Chromone-Pyrazolone/Benzofuranone Synthons: Access to Spiro-Pyrazolone/Benzofuranone-Hexahydroxanthone Hybrids

Abstract A DBU-catalyzed inter- and intramolecular double Michael addition of donor–acceptor chromone-pyrazolone/benzofuranone synthons and 3-methyl-4-nitro-5-alkenylisoxazoles has been established, which constructed structurally diverse spiro-pyrazolone/benzofuranone-hexahydroxanthone hybrids beari...

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Published in:Synthesis (Stuttgart) 2020-01, Vol.52 (1), p.85-97
Main Authors: Wei, Qi Di, Yao, Yi-Ming, Chang, Shun-Qin, Yang, Wu-De, Tian, Min-Yi, Liu, Xiong-Li, Zhou, Ying
Format: Article
Language:English
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Summary:Abstract A DBU-catalyzed inter- and intramolecular double Michael addition of donor–acceptor chromone-pyrazolone/benzofuranone synthons and 3-methyl-4-nitro-5-alkenylisoxazoles has been established, which constructed structurally diverse spiro-pyrazolone/benzofuranone-hexahydroxanthone hybrids bearing five consecutive stereocenters in good yields (up to 91%) with high diastereoselectivities (up to >20:1 dr). Moreover, this strategy further expanded the synthetic potential of bifunctional donor–acceptor chromones, and demonstrated great potential for applications in medicinal chemistry.
ISSN:0039-7881
1437-210X
DOI:10.1055/s-0037-1610728