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. 2011 Jul 20;16(7):6129-47.
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

Fatima Al-Omran  1 , Rafat M Mohareb, Adel Abou El-Khair
Affiliations

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 et al. Molecules. .

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.

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Figures

Scheme 1
Scheme 1
Synthesis of 2.
Figure 1
Figure 1
Perspective view and atom labeling of the X-ray structure of compound 2.
Scheme 2
Scheme 2
Syntheses of 4.
Figure 2
Figure 2
The complete assignment of H1 and 13C chemical shift for 4a based on the COSY, HSQC and HMBC experiments.
Figure 3
Figure 3
Perspective view and atom labeling of the X-ray structure of 4a.
Scheme 3
Scheme 3
Synthesis of compound 6.
Figure 4
Figure 4
Perspective view and atom labeling of the X-ray structure of 5.
Figure 5
Figure 5
13C-HSQC spectra for the compound 6 in DMSO-d6.
Figure 6
Figure 6
The complete assignment of H1 and 13C chemical shifts for 6 based on the COSY and HSQC experiments.
Scheme 4
Scheme 4
Synthesis of 9 and 10.
Figure 7
Figure 7
13C-HSQC spectra for the compound 10 in DMSO-d6.
Figure 8
Figure 8
The complete assignment of H1 and 13C chemical shifts for 10 based on the COSY and HSQC experiments.
Figure 9
Figure 9
Perspective view and atom labeling of the X-ray structure of 10.
See this image and copyright information in PMC

References

    1. Prabhu P.P, Pande S., Shastry C.S. Synthesis and Biological evaluation of of Schiff's bases of some new benzothiazole derivatives as antimicrobial agents. Int. J. Chem. Tech. Res. 2011;3:185–191.
    1. Alang G., kaur R., Kaur G., Singh A., Singla P. Synthesis and antibacterial activity of some new benzothiazole derivatives. Acta Pharm. Sci. 2010;52:213–218.
    1. Well G., Lowe R.P., Malcolm F., Steven G. Antitumer benzothiazoles. 13. (Diacetyloxy)- iodobenzene (DAIB) oxidation of 2-(4-hydroxy-3-methoxyphenyl)benzothiazole and related compounds in the presence of dienophiles. ARKIVOC. 2000:779–797.
    1. Devmurari V.P., Shivanand P., Goyani M.B., Nandanwar R.R., Jivani N.P., Perumal P. Synthesis and anticancer activity of some novel 2-substituted benzothiazole derivatives. Int. J. Chem. Tech. Res. 2010;2:681–689.
    1. Repicky A., Jantova S., Cipak L. Apoptosis induced by 2-acetyl-3-(6-methoxybenzothiazo)-2-yl-aminoacylonitrile in human leukemia cell involves ROS- mitochondrial mediated death signaling and activation of p38 MAPK. Cancer Lett. 2009;277:55–63. doi: 10.1016/j.canlet.2008.11.026. - DOI - PubMed

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