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Short Paper | Regular issue | Vol 83, No. 1, 2011, pp.99-106
Published online, 2nd December, 2010
DOI: 10.3987/COM-10-12071
An Efficient Synthesis of 3-Substituted 3H-Isobenzofuran-1-ylidenamines by the Reaction of 2-Cyanobenzaldehydes with Organolithiums and Their Conversion into Isobenzofuran-1(3H)-ones

Kazuhiro Kobayashi,* Kota Matsumoto, and Hisatoshi Konishi

*Department of Chemistry and Biotechnology, Graduate School of Engineering, Tottori University, 4-101 Koyama-minami, Tottori 680-8552, Japan

Abstract

A new and efficient synthesis of 3-substituted 3H-isobenzofuran-1-ylidenamines by the reaction of 2-cyanobenzaldehydes with nucleophiles, such as organolithiums or lithium enolates of t-butyl acetate and N,N-dimethylacetamide, is reported. Some of these products were converted into the corresponding 3-substituted isobenzofuran-1(3H)-ones (phthalides) upon treatment with hydrochloric acid in satisfactory yields.