Tandem oxidation/cyclization reaction of 4-(arylmethyl)oxy-2-diazobutyrate derivatives

Hideaki Kondo, Shuji Nagano, Hiroyuki Yamakoshi, Seiichi Nakamura

研究成果: Article査読

抄録

A tandem oxidation/cyclization reaction of γ-(arylmethyl)oxy-α-di-azobutyrate derivatives was investigated. While oxidative cleavage of the PMB ether was only observed upon treatment of an α-diazo-β-ketoester with DDQ, oxidation of α-diazo esters with an sp3 carbon at the β-position was accompanied by intramolecular attack of the diazo carbon atom and expulsion of the nitrogen gas to give 2,3-dihydrofurans in modest to good yields when an electron-withdrawing group was substituted at the β-position. Substrates bearing no electron-withdrawing β-substituent were found to give rearranged products, albeit in modest yields. A benzofuran derivative could also be obtained, although a hydroquinone adduct was formed as a byproduct.

本文言語English
ページ(範囲)894-915
ページ数22
ジャーナルHeterocycles
97
2
DOI
出版ステータスPublished - 2018
外部発表はい

ASJC Scopus subject areas

  • 分析化学
  • 薬理学
  • 有機化学

フィンガープリント

「Tandem oxidation/cyclization reaction of 4-(arylmethyl)oxy-2-diazobutyrate derivatives」の研究トピックを掘り下げます。これらがまとまってユニークなフィンガープリントを構成します。

引用スタイル