Chemistry of Polyhalogenated Nitrobutadienes, Part 9: Acyclic and Heterocyclic Nitroenamines and Nitroimines from 2-Nitroperchlorobuta-1,3-diene

Abstract

Various amino, diamino, aminothio, or benzotriazolo compounds derived from the exceedingly versatile 2-nitroperchlorobutadiene (1) gave structurally interesting and physiologically promising nitro-enamines, -imines, -amidines, and hydrazines as well as ring closure reaction products, e. g. pyrimidines and pyrazoles. Most of these reactions turned out to be highly selective with good to very good yields. The structure of the pyrazole precursor (E,E)-1-(benzotriazol-1-yl)-4,4-dichloro-3- (4-ethoxyphenylamino)-1-(4-ethoxyphenylimino)-2-nitrobut-2-ene (30), due to its exceptional substitution pattern, was evidenced by single-crystal X-ray diffraction analysis.