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Molecules 2011, 16(7), 6129-6147; https://doi.org/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

1
Department of Chemistry, Faculty of Science, Kuwait University, P.O. box 12613, safat 13060, Kuwait
2
Department of Chemistry, Faculty of Science, Cairo University, Giza, A.R., Egypt
3
Department of Organic Chemistry, Faculty of Pharmacy, October University for Modern Sciences and Arts, Elwahaat Road, October City, A.R., Egypt
*
Author to whom correspondence should be addressed.
Received: 21 June 2011 / Revised: 11 July 2011 / Accepted: 14 July 2011 / Published: 20 July 2011
(This article belongs to the Special Issue Heterocycles)
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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 (CC BY 3.0).
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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.

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