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Synthesis, Characterization and Crystal Structure of Some Novel 1‐Aryl‐2‐Thioxo‐2,3‐Dihydro‐1 H ‐Quinazolin‐4‐Ones
Author(s) -
Saeed Aamer,
Shaheen Uzma,
Bolte Michael
Publication year - 2010
Publication title -
journal of the chinese chemical society
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.329
H-Index - 45
eISSN - 2192-6549
pISSN - 0009-4536
DOI - 10.1002/jccs.201000013
Subject(s) - chemistry , intramolecular force , nucleophilic substitution , aryl , crystal structure , nucleophilic aromatic substitution , nucleophile , single crystal , stereochemistry , medicinal chemistry , crystallography , catalysis , organic chemistry , alkyl
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‐1 H ‐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 (S N Ar mechanism) rather than intramolecular aromatic substitution (S RN 1 mechanism).