Synthesis, characterization, crystal structure and supramolecularity of ethyl (E)-2-cyano-3-(3-methylthiophen-2-yl)acrylate and a new polymorph of ethyl (E)-2-cyano-3-(thiophen-2-yl)acrylate

Abstract

The synthesis, crystal structure and structural motif of two thiophene-based cyanoacrylate derivatives, namely, ethyl (E)-2-cyano-3-(3-methylthiophen-2-yl)acrylate (1), C11H11NO2S, and ethyl (E)-2-cyano-3-(thiophen-2-yl)acrylate (2), C10H9NO2S, are reported. Derivative 1 crystallized with two independent molecules in the asymmetric unit, and derivative 2 represents a new monoclinic (C2/m) polymorph. The molecular conformations of 1 and the two polymorphs of 2 are very similar, as all non-H atoms are planar except for the methyl of the ethyl groups. The intermolecular interactions and crystal packing of 1 and 2 are described and compared with that of the reported monoclinic (C2/m) polymorph of derivative 2 [Castro Agudelo et al. (2017). Acta Cryst. E73, 1287–1289].

Synthesis, characterization, antibacterial activity and cytotoxicity of (1′R,2′S,7a′S)‐2′‐(2,5‐dichlorothiophene‐3‐carbonyl)‐1′‐(aryl)‐1′,2′,5′,6′,7′,7a′‐hexahydrospiro[indoline‐3,3′‐pyrrolizin]‐2‐one derivatives

“…Therefore, for each compound, the reference molecule was selected as one having the R configuration at atom C18 ( 4e ) and C22 ( 4g , 4h ); on this basis, the configurations at atoms C6, C7, and C14 ( 4g and 4h ) are S, R and S, respectively. Bond distances and angles for the determined derivatives fall within the range reported for derivatives containing spiro[indoline‐3,3 ′ ‐pyrrolizin]‐2‐one [9, 10] and 2,5‐dichlorothiophene [19, 21, 22]. Selected geometrical parameters are listed in Table 2.…”

“…Additional studies of the synthesis of a diverse substituted spirooxindoles via 1,3‐dipolar cycloaddition reaction are reported [12–17]. In continuation to our work [18–24], we herein report the synthesis and characterization of (1′R,2′S,7a′S)‐2′‐(2,5‐dichlorothiophene‐3‐carbonyl)‐1′‐(aryl)‐1′,2′,5′,6′,7′,7a′‐hexahydrospiro[indoline‐3,3′‐pyrrolizin]‐2‐one, I , derivatives by the reaction of the corresponding 2,5‐dichlorothiophene containing chalcone (2,5‐dichlorothiophene has not been explored extensively), l ‐proline and 2,3‐indolinedione. The molecular, crystal structure and crystal supramolecularity of three derivatives, namely, (1′R,2′S,7a′S)‐1′‐(4‐(tert‐butyl)phenyl)‐2′‐(2,5‐dichlorothiophene‐3‐carbonyl)‐1′,2′,5′,6′,7′,7a′‐hexahydrospiro[indoline‐3,3′‐pyrrolizin]‐2‐one, (1′R,2′S,7a′S)‐2′‐(2,5‐dichlorothiophene‐3‐carbonyl)‐1′‐(4‐fluorophenyl)‐1′,2′,5′,6′,7′,7a′‐hexahydrospiro[indoline‐3,3′‐pyrrolizin]‐2‐one and (1′R,2′S,7a′S)‐1′‐(3‐Chlorophenyl)‐2′‐(2,5‐dichlorothiophene‐3‐carbonyl)‐1′,2′,5′,6′,7′,7a′‐hexahydrospiro[indoline‐3,3′‐pyrrolizin]‐2‐one are also reported.…”

Nanographene‐Doped Chalcone Derivatives of Dioxybiphenyl‐Bridged Dispirocyclotriphosphazenes: Synthesis, Electrical Properties, and DFT Calculations

“…Another factor that makes these compounds important is their use as intermediates for the synthesis of important heterocyclic substances with very high chemical stability and biological properties. Different biologically active heterocyclic compounds such as aurone, [10] flavone, [11] pyrazole, [12] pyrazoline, [13] pyridine, [14] benzodiazepine, [15] and pyrimidines [16] can be prepared with chalcones. In addition, there are studies in which the electrochemical and physical properties of chalcones containing organometallic functional groups are very remarkable [17] .…”

Crystal Structure of 2-(Ethoxymethylene)malononitrile and DFT Evaluation of the C-H···N≡C Close Contacts Energy

“…Also, this compound is assumed to be an intermediate in different three-component reactions [4]. There are, in the literature, a few mentions about the crystal structures of structurally related compounds with nitrile groups, namely, ethyl (E)-2-cyano-3-(thiophen-2-yl)acrylate [5] and (E)-ethyl-2-cyano-3-(furan-2-yl)acrylate [6]. To the best of our knowledge, there is no information about the crystal structure of (1).…”