Synthesis and Crystal Structure of 1-(3-Fluorophenyl)-2-thioxo-2,3-dihydroquinazolin-4(1H)-one

Abstract

Abstract:The base catalyzed intramolecular nucleophilic cyclization of 1-(2-bromobenzoyl)-3-(2-fluorophenyl)thiourea (1) in the presence of N,N-dimethyl formamide (DMF) afforded the 1-(3-fluorophenyl)-2-thioxo-2,3-dihydroquinazolin-4(1H)-one (2) by an intramolecular nucleophilic substitution S N Ar mechanism. The structure was supported by the spectroscopic data and unambiguously confirmed by the single crystal Xray diffraction data. It crystallizes in the orthorhombic space group P na2 1 with unit cell dimensions a = 22.430(4), b = 8.1478(16), c = 13.522(3) Å, V = 2471.2(9) Å 3 . There are two independent molecules per asymmetric unit that are linked to centrosymmetric ABdimers via intermolecular N-H…S bonds.

KF/Al2O3 Catalyzed One-Pot Three-Component Process for the Synthesis of Some 2-Thioxoquinazolin-4(1H)-one Derivatives

“…The quinazolinones scaffold are important class of fused heterocycles with a show promise such as antiinflammatory 4 , antimalarial 5 , anti HIV 6 and anti cancer 7 and dihydrofolate reductase inhibitors 8 . Moreover, few methods are reported for the synthesis of 2-thioxoquinazolin-4-ones, as most of the methods reported are for quinazolin-2,4(1H,3H)diones 9,10 .…”