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

Fatima Al-Omran; Rafat M Mohareb; Adel Abou El-Khair

doi:10.3390/molecules16076129

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

Molecules. 2011 Jul 20;16(7):6129-47. doi: 10.3390/molecules16076129.

Authors

Fatima Al-Omran¹, Rafat M Mohareb, Adel Abou El-Khair

Affiliation

¹ Department of Chemistry, Faculty of Science, Kuwait University, P.O. box 12613, Safat 13060, Kuwait. fatima.alomran@ ku.edu.kw

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.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Acrylonitrile / chemistry*
Benzimidazoles / chemistry*
Benzothiazoles / chemistry*
Magnetic Resonance Spectroscopy
Molecular Structure
X-Ray Diffraction

Substances

Benzimidazoles
Benzothiazoles
2-mercaptobenzimidazole
benzothiazole
Acrylonitrile