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Synlett 2020; 31(02): 189-193
DOI: 10.1055/s-0039-1691491
letter
© Georg Thieme Verlag Stuttgart · New York

One-Pot Deprotonative Synthesis of Biarylazacyclooctynones

Yuto Hioki
a   Department of Chemical Science and Engineering, Kobe University, Rokkodai, Nada, Kobe 657-8501, Japan   Email: okano@harbor.kobe-u.ac.jp
,
Mayu Itoh
a   Department of Chemical Science and Engineering, Kobe University, Rokkodai, Nada, Kobe 657-8501, Japan   Email: okano@harbor.kobe-u.ac.jp
,
Atsunori Mori
a   Department of Chemical Science and Engineering, Kobe University, Rokkodai, Nada, Kobe 657-8501, Japan   Email: okano@harbor.kobe-u.ac.jp
b   Research Center for Membrane and Film Technology, Kobe University, Rokkodai, Nada, Kobe 657-8501, Japan
,
Kentaro Okano  ∗
a   Department of Chemical Science and Engineering, Kobe University, Rokkodai, Nada, Kobe 657-8501, Japan   Email: okano@harbor.kobe-u.ac.jp
› Author AffiliationsThis work was financially supported by the Japan Society for the Promotion of Science (JSPS KAKENHI, Grant Numbers JP16K05774 in Scientific Research (C), JP19H02717 in Scientific Research (B), JP16H01153 and JP18H04413 in the Middle Molecular Strategy) and the Japan Society for the Promotion of Science (JSPS) predoctoral fellowship (for Y.H.).
Further Information

Publication History

Received: 10 October 2019

Accepted after revision: 04 November 2019

Publication Date:
04 December 2019 (online)

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Abstract

Deprotonative formation of biarylazacyclooctynone (BARAC) from the corresponding enol triflate is described. The reaction furnished the azacyclooctynone within one hour at –78 °C. This process could be performed in one pot from the starting ketone to provide a range of BARAC derivatives in moderate to excellent yields. The protocol enabled the gram-scale formation of the BARAC skeleton by reducing the number of reaction steps. Furthermore, the established method was applied to the synthesis of the BARAC derivative bearing a coumarin moiety.

Key words

alkynes - bioorganic chemistry - enolate - one-pot reaction - strained molecules

Supporting Information

    Supporting information for this article is available online at https://doi.org/10.1055/s-0039-1691491.
  • Supporting Information
 

  • References and Notes

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