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Molecules 2011, 16(7), 6129-6147; doi:10.3390/molecules16076129
Article

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

1,* , 2,3 and 1
Received: 21 June 2011; in revised form: 11 July 2011 / Accepted: 14 July 2011 / Published: 20 July 2011
(This article belongs to the Special Issue Heterocycles)
Download PDF [870 KB, uploaded 18 June 2014]
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.
Keywords: benzothiazole; 2-mercaptobenazothiazole; 3-phenylquinazolin-4(3H)-one; methyl vinyl ketone; acrylonitrile benzothiazole; 2-mercaptobenazothiazole; 3-phenylquinazolin-4(3H)-one; methyl vinyl ketone; acrylonitrile
This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.

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MDPI and ACS Style

Al-Omran, F.; Mohareb, R.M.; El-Khair, A.A. 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, 16, 6129-6147.

AMA Style

Al-Omran F, Mohareb RM, El-Khair AA. 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; 16(7):6129-6147.

Chicago/Turabian Style

Al-Omran, Fatima; Mohareb, Rafat M.; El-Khair, Adel Abou. 2011. "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 16, no. 7: 6129-6147.


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