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Issue 9, 2018
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One step synthesis of a fused four-ring heterocycle

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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

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Article information

05 Feb 2018
06 Apr 2018
First published
12 Apr 2018

New J. Chem., 2018,42, 7125-7129
Article type
Author version available

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

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