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Communication | Regular issue | Vol 87, No. 8, 2013, pp.1691-1698
Published online, 4th July, 2013
DOI: 10.3987/COM-13-12755
Novel Photosensitized Cyclization Reactions of Ethyl 3-Amino-3-phenyl-2-propenoate Derivatives to Highly Substituted Pyrroles

Yohsuke Ishida, Yuhki Yoshida, Tetsutaro Igarashi, and Tadamitsu Sakurai*

*Department of Material and Life Chemistry, Faculty of Engineering, Kanagawa University, 3-27-1 Rokkakubashi, Kanagawa-ku, Yokohama 221-8686, Japan


Irradiation of nitrogen-saturated acetonitrile solutions containing ethyl 3-amino-3-phenyl-2-propenoate derivatives with the (Z)-configuration [(Z)-1] and 10-methylacridinium perchlorate (MAP) at wavelengths longer than 340 nm afforded the corresponding pyrrole derivatives in good to high yields without exhibiting a profound effect related to the substituents. An analysis of the Stern–Volmer plots for the fluorescence quenching of MAP by (Z)-1 showed that this sensitizer fluorescence is efficiently quenched, and hence electron transfer is confirmed to be involved in the primary process of the MAP-sensitized cyclization reactions of 1.