Synthesis of New Dibenzo-tetraaza and Dibenzo-dioxadiaza[14]annulene Derivatives Using 3-Bromo-substituted Vinamidinium Salt

Abstract

Novel bromo-substituted derivatives of dibenzo-tetraaza and dibenzo-dioxadiaza[14]annulenes B–G were synthesized by a twofold condensation reaction of a symmetrical bromo-substituted vinamidinum salt A with ortho-diamino- and ortho-amino-hydroxyarenes such as 1,2-diaminobenzene, 1,2-diamino-4,5-dimethylbenzene, 2,3-diaminonaphthalene, 1,2-diamino-4-methylbenzene, 2-amino-1-hydroxybnzene, and 2-amino-1-hydroxy-5-methyl-benzene in acetonitrile/acetic acid as reaction medium. The ultraviolet/visible spectral behavior of these [14]annulenes was examined in dimethyl sulfoxide (DMSO). Elemental analysis, infrared, ¹H NMR, ¹³C NMR, and mass spectra confirm the molecular structure of the newly synthesized compounds.

GRAPHICAL ABSTRACT

Keywords:

• Aromatic amines
• 6,13-dibromo-1,4,8,11-tetraaza[14]annulene derivatives
• 3-bromo vinamidinium salt

ACKNOWLEDGMENT

Financial support of this work by the Research Council of the Persian Gulf University is gratefully acknowledged.