Jump to main content
Jump to site search

Issue 9, 2018
Previous Article Next Article

One step synthesis of a fused four-ring heterocycle

Author affiliations


A wide range of natural biomolecules and pharmaceuticals are nitrogen rich heterocycles. Though preparation of fused multi-ring systems typically requires multiple synthetic steps, 13-imino-7,13-dihydro-6H-quinazolino[3,4-a]quinazolin-6-one (IDQQ) was serendipitously obtained in one step from commercially available phenylic precursors. Single crystal X-ray diffraction, 1H-NMR and density functional theory calculations (DFT/B3LYP/6-31G(d,p)) were used in combination to unambiguously assign the major tautomer present in the monoclinic crystals. IDQQ appears to be the product of a thermodynamically-driven solution rearrangement of a key intermediate, 1,3-bis(o-cyanophenyl)urea. This type of cyclization may be an efficient method for the formation of other related heterocycles.

Graphical abstract: One step synthesis of a fused four-ring heterocycle

Back to tab navigation

Supplementary files

Publication details

The article was received on 05 Feb 2018, accepted on 06 Apr 2018 and first published on 12 Apr 2018

Article type: Paper
DOI: 10.1039/C8NJ00629F
Author version

Download author version (PDF)
New J. Chem., 2018,42, 7125-7129

  •   Request permissions

    One step synthesis of a fused four-ring heterocycle

    M. A. Solomos, J. A. Bertke and J. A. Swift, New J. Chem., 2018, 42, 7125
    DOI: 10.1039/C8NJ00629F

Search articles by author