Marina A. Solomos

One step synthesis of a fused four-ring heterocycle

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.

CCDC 1554299: Experimental Crystal Structure Determination

Related Article: Marina A. Solomos, Taylor A. Watts, Jennifer A. Swift|2017|Cryst.Growth Des.|||doi:10.1021/acs.cgd.7b00922

CCDC 1504101: Experimental Crystal Structure Determination

Related Article: Marina A. Solomos, Taylor A. Watts, Jennifer A. Swift|2017|Cryst.Growth Des.|||doi:10.1021/acs.cgd.7b00757

CCDC 1504133: Experimental Crystal Structure Determination

Related Article: Marina A. Solomos, Taylor A. Watts, Jennifer A. Swift|2017|Cryst.Growth Des.|||doi:10.1021/acs.cgd.7b00757

CCDC 1504102: Experimental Crystal Structure Determination

Related Article: Marina A. Solomos, Taylor A. Watts, Jennifer A. Swift|2017|Cryst.Growth Des.|||doi:10.1021/acs.cgd.7b00757

CCDC 1504105: Experimental Crystal Structure Determination

Related Article: Marina A. Solomos, Taylor A. Watts, Jennifer A. Swift|2017|Cryst.Growth Des.|||doi:10.1021/acs.cgd.7b00757

CCDC 1504103: Experimental Crystal Structure Determination

Related Article: Marina A. Solomos, Taylor A. Watts, Jennifer A. Swift|2017|Cryst.Growth Des.|||doi:10.1021/acs.cgd.7b00757

Crystal structure of a di­aryl carbonate: 1,3-phenyl­ene bis­(phenyl carbonate)

The whole molecule of the title diarylcarbonate is generated by mirror symmetry, the mirror bisecting the central benzene ring, and the carbonate groups adopt an s-cis-s-cis conformation. In the crystal, there are only weak C—H⋯O hydrogen bonds and offset π–π interactions present.