title: Synthesis and E/Z configuration determination of novel derivatives of 3-aryl-2-(benzothiazol-2'-ylthio) acrylonitrile, 3-(benzothiazol-2'-ylthio)-4-(furan-2''-yl)-3-buten-2-one and 2-(1-(furan-2''-yl)-3'-oxobut-1''-en-2-ylthio)-3-phenylquinazolin-4(3H)-one.
abstract: Knoevenagel condensation of 2-(benzothiazol-2-ylthio) acetonitrile (2) with either furan-2-carbaldehyde or thiophene-2-carbaldehydes leads to E-isomers 4a-b exclusively, while the condensation of the compound 2 with benzaldehyde or para-substituted benzaldehydes with an electron-donating group afforded E/Z mixtures 4c-e with preferentially formation of the E-isomer. Condensation of furan-2-carbaldehyde (3a) with either 1-(benzothiazol-2'-ylthio) propan-2-one (5) or 2-(2'-oxo propylthio)-3-phenyl-quinazolin-4(3H)-one (9) leads exclusively to the Z-isomers of 6 and 10, respectively. The structures of the newly synthesized compounds were elucidated by elemental analyses, ¹H-NMR and ¹³C-NMR spectra, COSY, HSQC, HMBC, NOE, MS and X-ray crystallographic investigations.
authors.affiliation: Department of Chemistry, Faculty of Science, Kuwait University, P.O. box 12613, Safat 13060, Kuwait. fatima.alomran@ ku.edu.kw
authors.forename: Fatima
authors.initials: F
authors.lastname: Al-Omran
authors.forename: Rafat M
authors.initials: RM
authors.lastname: Mohareb
authors.forename: Adel Abou
authors.initials: AA
authors.lastname: El-Khair
mesh_terms: D000181:Acrylonitrile / Q000737:chemistry*; D001562:Benzimidazoles / Q000737:chemistry*; D052160:Benzothiazoles / Q000737:chemistry*; D009682:Magnetic Resonance Spectroscopy; D015394:Molecular Structure; D014961:X-Ray Diffraction
chemical_list: D001562:Benzimidazoles; D052160:Benzothiazoles; C030698:2-mercaptobenzimidazole; C005465:benzothiazole; D000181:Acrylonitrile