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

Hideaki Kondo, Shuji Nagano, Hiroyuki Yamakoshi, Seiichi Nakamura

Research output: Contribution to journalArticlepeer-review

Abstract

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.

Original languageEnglish
Pages (from-to)894-915
Number of pages22
JournalHeterocycles
Volume97
Issue number2
DOIs
Publication statusPublished - 2018
Externally publishedYes

ASJC Scopus subject areas

  • Analytical Chemistry
  • Pharmacology
  • Organic Chemistry

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