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Regiospecific construction of diverse and polyfunctionalized γ-pyrone cores by indium(III)-catalyzed annulation of diazodicarbonyls with active methylenes, 4-hydroxycoumarins, or 4-hydroxyquinolinone

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Abstract

An efficient and novel construction of diverse and polyfunctionalized γ-pyrones has been developed by InBr3-catalyzed annulation of various cyclic and acyclic diazo compounds with multifarious active methylenes, 4-hydroxycoumarins, or 4-hydroxyquinolinone. This technique proceeds through a cascade of carbene generation/ketene formation/conjugate addition/intramolecular cyclization/elimination reactions. In addition, transformation of the synthesized compound for further functionalization is realized.

Graphical abstract: Regiospecific construction of diverse and polyfunctionalized γ-pyrone cores by indium(iii)-catalyzed annulation of diazodicarbonyls with active methylenes, 4-hydroxycoumarins, or 4-hydroxyquinolinone

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Publication details

The article was received on 18 Sep 2018, accepted on 22 Oct 2018 and first published on 22 Oct 2018


Article type: Research Article
DOI: 10.1039/C8QO01006D
Citation: Org. Chem. Front., 2018, Advance Article
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    Regiospecific construction of diverse and polyfunctionalized γ-pyrone cores by indium(III)-catalyzed annulation of diazodicarbonyls with active methylenes, 4-hydroxycoumarins, or 4-hydroxyquinolinone

    S. M. B. Maezono, G. E. Park and Y. R. Lee, Org. Chem. Front., 2018, Advance Article , DOI: 10.1039/C8QO01006D

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