PREPARATION AND STEREOCHEMISTRY OF DIOXATETRAAZAPERHYDROANTHRACENES AND DIOXATETRAAZAPERHYDROPERYLENES FROM THE REACTION OF 2-HYDRAZINOETHANOLS WITH ALDEHYDES AND GLUTARALDEHYDE

Hydrazinoethanols 1 were reacted with aldehydes 2 and 6 and glutaralde hyde (14) in aqueous solution to give dioxatetraazaperhydroanthracenes 3, 7, 12, and 13 and -perylenes 15 in yields of 19-88 and 42-72%, res pectively. Compounds 3, 7, 12, and 15 were deduced by C-13-NMR spectra to have two C-2 symmetry axes, while compound 12 was shown to have a symmetry axis by X-ray crystallography. The most favorable stereoisome rs were consistent with predictions obtained by the semiempirical mole cular orbital method AM1. The structure of compound 15 was confirmed b y X-ray crystallography.