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Paper | Special issue | Vol 90, No. 2, 2015, pp. 1158 - 1167
Published online: 19th August, 2014
DOI: 10.3987/COM-14-S(K)91
4,8-Dihydropyrrol[3,4-f]isoindole as a Useful Building Block for Near-Infrared Dyes

Hidemitsu Uno,* Mitsunori Nakamura, Kazuki Jodai, Shigeki Mori, and Tetsuo Okujima

*Department of Chemistry and Biology, Graduate School or Science and Engineering, Ehime University, Bunkyo-cho 2-5, Matsuyama 790-8577, Japan

Abstract

4,8-Dihydropyrrol[3,4-f]isoindole was prepared from 4,7-dihydroisoindole based on the modified Barton-Zard reaction. Addition of phenylsulfenyl chloride followed by oxidation and dehydrochlorination gave phenylsulfonyldihydroisoindole, which underwent the smooth reaction with an isocyanoacetate under basic conditions to give 4,8-dihydropyrrol[3,4-f]isoindole-1,5- and 1,7-dicarboxylates in good yields. The pyrrolisoindole was successfully converted to the benzene-fused bisBODIPY, absorption maximum of which was 758 nm.

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