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Paper | Regular issue | Vol 78, No. 2, 2009, pp.397-413
Published online, 9th October, 2008
DOI: 10.3987/COM-08-11515
■ Synthesis of Unusual Naphtho[2,1-b]furans and Novel 1H-Benz[e]indolinones via Selective Intramolecular Cyclization

Zhi-qi Cong and Hiroshi Nishino*

*Department of Chemistry, Graduate School of Science and Technology, Kumamoto University, Kurokami 2-39-1, Kumamoto 860-8555, Japan

Abstract

The 2-(2-methoxy-1-naphthyl)-3-oxobutanamides were treated with concentrated hydrochloric acid in acetic acid at room temperature to exclusively give the unusual 5-chloronaphtho[2,1-b]furans in moderate to excellent yields. The same reaction was carried out in ethylene glycol at 80 °C to selectively produce the novel 1H-benz[e]indolinones in good yields. The characterization of the products and the reaction pathway of the selective intramolecular cyclization were discussed.