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Communication | Regular issue | Vol 9, No. 7, 1978, pp.813-818
Published online, 1st January, 1970
DOI: 10.3987/R-1978-07-0813
A Convenient Photosynthesis of Heterocyclic Quinones by a One-pot Reaction

Mitsuo Akiba,* Satoshi Ikuta, and Toyozo Takada

*School of Pharmacy, Tokyo University of Pharmacy and Life Science, 1432-1 Horinouchi, Hachioji, Tokyo 192-0392, Japan

Abstract

The photochemical reaction of 2-chloro-3-acetylethoxycarbonylmethyl-1,4-naphthoquinone (1b) with various secondary amines (pyrrolidine, piperidine, morpholine, and hexamethyleneimine) provided a convenient, one-pot, preparative route to the heterocyclic quinones (4b) as a mixture of stereoisomers due to the different substituents. A similar photoreaction of 2-chloro-3-ethoxycarbonylcyanomethyl-1,4-naphthoquinone (1c) with amines gave selectively one diastereomer of the series (4c).
The stereochemical studies on these photoproducts were investigated by using the europium-shifted spectra.