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Synthesis, Characterization And Crystal Structure Of Some Novel 1-Aryl-2-Thioxo-2,3-Dihydro-1H-Quinazolin-4-Ones

A. Saeed, Uzma Shaheen, M. Bolte
Published 2010 · Chemistry

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The base catalyzed intramolecular nucleophilic cyclization of 1-(2-haloaroyl)-3-aryl thioureas (1a-i), in the presence of DMF afforded the 1-aryl-2-thioxo-2,3-dihydro-1H-quinazolin-4-ones (2a-i). The structures were confirmed by spectroscopic data, elemental analyses and in case of the 2c by single crystal X-ray diffraction data. The mechanistic studies support an intramolecular nucleophilic substitution (SNAr mechanism) rather than intramolecular aromatic substitution (SRN1 mechanism).
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