2-(3-Pyrrolin-1-yl)-1,4-naphthoquinones: Photoactivated Alkylating Agents

The preparation of 2-(3-pyrrolin-1-yl)-1,4-naphthoquinones and a study of their use as photoactivated alkylating agents is reported. The title compounds were easily synthesized by conjugate addition of the corresponding 3-pyrrolines to various naphthoquinones. Upon exposure to ambient room light, the compounds undergo an internal redox reaction to form 2-(pyrrol-1-yl)-1,4-hydroquinones, which are activated for nucleophilic addition by an S N 1 azafulvene mechanism. Control experiments demonstrated that the redox reaction is triggered by light and that the nucleophilic addition does not proceed before this activation occurs.(© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2008)Peer Reviewedhttp://deepblue.lib.umich.edu/bitstream/2027.42/60962/1/4264_ftp.pd