Literature DB >> 18057629

(Z)-3-(Benzo[b]thiophen-2-yl)-2-(3,4,5-trimethoxyphenyl)acrylonitrile and (E)-3-(benzo[b]thiophen-2-yl)-2-(3,4-dimethoxyphenyl)acrylonitrile. [corrected].

Vijayakumar N Sonar1, Sean Parkin, Peter A Crooks.   

Abstract

The title compounds, C20H17NO3S, (I), and C19H15NO2S, (II), were prepared by the reaction of benzo[b]thiophene-2-carbaldehyde with (3,4,5-trimethoxyphenyl)acetonitrile and (3,4-dimethoxyphenyl)acetonitrile, respectively, in the presence of methanolic potassium hydroxide. In (I), the C=C bond linking the benzo[b]thiophene and the 3,4,5-trimethoxyphenyl units has E geometry, with dihedral angles between the plane of the bridging unit and the planes of the two adjacent ring systems of 5.2 (3) and 13.1 (2) degrees, respectively. However, in (II), the C=C bond has Z geometry, with dihedral angles between the plane of the bridging unit and the planes of the adjacent benzo[b]thiophene and 3,4-dimethoxyphenyl units of 4.84 (17) and 76.09 (7) degrees, respectively. There are no significant intermolecular hydrogen-bonding interactions in the packing of (I) and (II). The packing is essentially stabilized via van der Waals forces.

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Year:  2007        PMID: 18057629     DOI: 10.1107/S0108270107054959

Source DB:  PubMed          Journal:  Acta Crystallogr C        ISSN: 0108-2701            Impact factor:   1.172


  5 in total

1.  Synthesis and evaluation of a series of benzothiophene acrylonitrile analogs as anticancer agents.

Authors:  Narsimha Reddy Penthala; Vijayakumar N Sonar; Jamie Horn; Markos Leggas; Jai Shankar K B Yadlapalli; Peter A Crooks
Journal:  Medchemcomm       Date:  2013-07-01       Impact factor: 3.597

2.  (Z)-3-(1H-Indol-3-yl)-2-(3,4,5-tri-methoxy-phen-yl)acrylonitrile.

Authors:  Narsimha Reddy Penthala; Sean Parkin; Peter A Crooks
Journal:  Acta Crystallogr Sect E Struct Rep Online       Date:  2012-02-17

3.  (Z)-3-(1-Benzofuran-2-yl)-2-(3,4,5-tri-meth-oxy-phen-yl)acrylonitrile.

Authors:  Narsimha Reddy Penthala; Sean Parkin; Peter A Crooks
Journal:  Acta Crystallogr Sect E Struct Rep Online       Date:  2012-02-17

4.  Crystal structures of (Z)-5-[2-(benzo[b]thio-phen-2-yl)-1-(3,5-di-meth-oxy-phen-yl)ethen-yl]-1H-tetra-zole and (Z)-5-[2-(benzo[b]thio-phen-3-yl)-1-(3,4,5-tri-meth-oxy-phen-yl)ethen-yl]-1H-tetra-zole.

Authors:  Narsimha Reddy Penthala; Jaishankar K B Yadlapalli; Sean Parkin; Peter A Crooks
Journal:  Acta Crystallogr E Crystallogr Commun       Date:  2016-04-08

5.  Comparison of crystal structures of 4-(benzo[b]thio-phen-2-yl)-5-(3,4,5-tri-meth-oxy-phen-yl)-2H-1,2,3-triazole and 4-(benzo[b]thio-phen-2-yl)-2-methyl-5-(3,4,5-tri-meth-oxy-phen-yl)-2H-1,2,3-triazole.

Authors:  Narsimha Reddy Penthala; Nikhil Reddy Madadi; Shobanbabu Bommagani; Sean Parkin; Peter A Crooks
Journal:  Acta Crystallogr Sect E Struct Rep Online       Date:  2014-10-24
  5 in total

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