Conversion of di-aryl-chalcones into 4,5-di-hydro-pyrazole-1-carbo-thio-amides: mol-ecular and supra-molecular structures of two precursors and three products

Acta Crystallographica. Section E, Crystallographic Communications
Mohammed A E ShaibahChristopher Glidewell

Abstract

Chalcones of type 4-XC6H4C(O)CH=CHC6H4(OCH2CCH)-4, where X = Cl, Br or MeO, have been converted to the corresponding 4,5-di-hydro-pyrazole-1-carbo-thio-amides using a cyclo-condensation reaction with thio-semicarbazide. The chalcones 1-(4-chloro-phen-yl)-3-[4-(prop-2-yn-yloxy)phen-yl]prop-2-en-1-one, C18H13ClO2, (I), and 1-(4-bromo-phen-yl)-3-[4-(prop-2-yn-yloxy)phen-yl]prop-2-en-1-one, C18H13BrO2, (II), are isomorphous, and their mol-ecules are linked into sheets by two independent C-H⋯π(arene) inter-actions, both involving the same aryl ring with one C-H donor approaching each face. In each of the products (RS)-3-(4-chloro-phen-yl)-5-[4-(prop-2-yn-yloxy)phen-yl]-4,5-di-hydro-pyrazole-1-carbo-thio-amide, C19H16ClN3OS, (IV), (RS)-3-(4-bromo-phen-yl)-5-[4-(prop-2-yn-yloxy)phen-yl]-4,5-di-hydro-pyrazole-1-carbo-thio-amide, C19H16BrN3OS, (V), and (RS)-3-(4-meth-oxy-phen-yl)-5-[4-(prop-2-yn-yloxy)phen-yl]-4,5-di-hydro-pyrazole-1-carbo-thio-amide, C20H19N3O2S, (VI), the reduced pyrazole ring adopts an envelope conformation with the C atom bearing the 4-prop-2-yn-yloxy)phenyl substituent, which occupies the axial site, displaced from the plane of the four ring atoms. Compounds (IV) and (V) are isomorphous and their mol-ecules are lin...Continue Reading

References

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Jan 5, 2010·Bioorganic & Medicinal Chemistry Letters·Renate H HansKelly Chibale
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Jan 9, 2015·Acta Crystallographica. Section C, Structural Chemistry·George M Sheldrick
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Apr 23, 2016·European Journal of Medicinal Chemistry·Bin YuHong-Min Liu
Dec 25, 2016·European Journal of Medicinal Chemistry·Pinki YadavShashi Bhushan
Oct 6, 2017·Acta Crystallographica. Section C, Structural Chemistry·Viviana CuartasChristopher Glidewell
Jan 13, 2018·Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry·Khalid KarrouchiM'hammed Ansar
Jan 11, 2020·Acta Crystallographica. Section E, Crystallographic Communications·Anthony L Spek

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Citations

Oct 30, 2020·Acta Crystallographica. Section E, Crystallographic Communications·Tharangini K ShreekanthChristopher Glidewell
Feb 2, 2021·Acta Crystallographica. Section E, Crystallographic Communications·Sreeramapura D ArchanaChristopher Glidewell

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Methods Mentioned

BETA
X-ray
neutron diffraction

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