title: Preparation and Stereochemistry of Dioxatetraazaperhydroanthracenes and -perylenes from the Reaction of 2-Hydrazinoethanols with Aldehydes and Glutaraldehyde.
abstract: Hydrazinoethanols 1 were reacted with aldehydes 2 and 6 and glutaraldehyde (14) in aqueous solution to give dioxatetraazaperhydroanthracenes 3, 7, 12, and 13 and -perylenes 15 in yields of 19-88 and 42-72%, respectively. Compounds 3, 7, 12, and 15 were deduced by (13)C-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 stereoisomers were consistent with predictions obtained by the semiempirical molecular orbital method AM1. The structure of compound 15 was confirmed by X-ray crystallography.
authors.affiliation: Faculty of Pharmaceutical Sciences, Kumamoto University, Oe-hon-machi, Kumamoto 862, Japan.
authors.forename: Tadashi
authors.initials: T
authors.lastname: Okawara
authors.forename: Shuji
authors.initials: S
authors.lastname: Ehara
authors.forename: Hideaki
authors.initials: H
authors.lastname: Kagotani
authors.forename: Yoshinari
authors.initials: Y
authors.lastname: Okamoto
authors.forename: Masashi
authors.initials: M
authors.lastname: Eto
authors.forename: Kazunobu
authors.initials: K
authors.lastname: Harano
authors.forename: Tetsuo
authors.initials: T
authors.lastname: Yamasaki
authors.forename: Mitsuru
authors.initials: M
authors.lastname: Furukawa