@article{be736559901246a983e1c1db09fa0f1a,
title = "Tandem oxidation/cyclization reaction of 4-(arylmethyl)oxy-2-diazobutyrate derivatives",
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.",
author = "Hideaki Kondo and Shuji Nagano and Hiroyuki Yamakoshi and Seiichi Nakamura",
note = "Funding Information: This research was supported in part by a Grant-in-Aid for Scientific Research from the Japan Society for the Promotion of Science (JSPS) and the Platform Project for Supporting in Drug Discovery and Life Science Research from Japan Agency for Medical Research and Development (AMED). We are grateful to Dr. Kotaro Kikushima and Ms. Ayaka Kimura for assisting in the preparation of substrates. We thank Dr. Kan'ichiro Ishiuchi of the Graduate School of Pharmaceutical Sciences, Nagoya City University for helpful discussion on stereochemical assignments. Publisher Copyright: {\textcopyright} 2018 The Japan Institute of Heterocyclic Chemistry.",
year = "2018",
doi = "10.3987/COM-18-S(T)67",
language = "English",
volume = "97",
pages = "894--915",
journal = "Heterocycles",
issn = "0385-5414",
publisher = "Japan Institute of Heterocyclic Chemistry",
number = "2",
}