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Paper | Special issue | Vol 97, No. 2, 2018, pp.894-915
Published online, 19th April, 2018
DOI: 10.3987/COM-18-S(T)67
Tandem Oxidation/Cyclization Reaction of 4-(Arylmethyl)oxy-2-diazobutyrate Derivatives

Hideaki Kondo, Shuji Nagano, Hiroyuki Yamakoshi, and Seiichi Nakamura*

*Graduate School of Pharmaceutical Sciences, Nagoya City University, 3-1 Tanabe-dori, Mizuho-ku, Nagoya 467-8603, Japan

Abstract

A tandem oxidation/cyclization reaction of γ-(arylmethyl)oxy-α-diazobutyrate 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.