Chemo- and Diastereoselective Synthesis of Spirooxindole-pyrazolines and Pyrazolones via P(NMe2)(3)-Mediated Substrate-Controlled Annulations of Azoalkenes with alpha;-Dicarbonyl Compounds

P(NMe2)(3)-mediated substrate-controlledannulationsof azoalkenes with & alpha;-dicarbonyl compounds are reported, wherethe azoalkenes serve as either four or five-atom synthons chemoselectively.The azoalkene participates in annulation with isatins as a four-atomsynthon to furnish the spirooxindo...

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Published inOrganic letters Vol. 25; no. 26; pp. 4776 - 4781
Main Authors Du, Yunfeng, Liu, Yuefei, Guo, Hongyu, Liu, Rongfang, Zhou, Rong
Format Journal Article
LanguageEnglish
Published WASHINGTON Amer Chemical Soc 26.06.2023
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
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FACILE SYNTHESIS
OXINDOLES
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Summary:P(NMe2)(3)-mediated substrate-controlledannulationsof azoalkenes with & alpha;-dicarbonyl compounds are reported, wherethe azoalkenes serve as either four or five-atom synthons chemoselectively.The azoalkene participates in annulation with isatins as a four-atomsynthon to furnish the spirooxindole-pyrazolines, whereas it functionsas a novel five-atom synthon in annulation with aroylformates, therebyleading to chemo- and stereoselective formation of pyrazolones. Thesynthetic utilities of the annulations have been demonstrated, anda novel TEMPO-mediated decarbonylation reaction is unveiled.
ISSN:1523-7060
1523-7052
DOI:10.1021/acs.orglett.3c01348