Synthesis and Molecular Structure Characterization of Novel 1,6-Diazahexatrienes

Abstract

Novel 1,6-diazahexatrienes (1a–d) are a type of aza-conjugated hexatriene containing N,N-diamino moieties. We present the oxidative dimerization of 1,1,2-trisubstituted hydrazines as a synthetic approach to 1,6-diazahexatriene derivatives, rather than the expected pyrazine and pyridazine. The proposed mechanism for formation of 1a–d involves oxidative dimerization of 1,1,2-trisubstituted hydrazines via their hydrazones. The structures of 1a–d were characterized by ¹H NMR, ¹³C NMR, and mass spectroscopy. A detailed discussion regarding the character of the three-dimensional structure of 1 is based on x-ray crystallography.

GRAPHICAL ABSTRACT

Keywords:

• 1,6-Diazahexatriene
• oxidative dimerization
• 1,1,2-trisubstituted hydrazines

SUPPLEMENTAL MATERIAL

Experimental procedures, ¹H NMR and ¹³C NMR spectra data, x-ray diffraction data, and references for all the products for this article can be accessed on the publisher’s website.