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Phosphorus, Sulfur, and Silicon and the Related Elements Volume 194, 2019 - Issue 11
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Original Articles

Design and synthesis of some new thiophene and 1,3,4-thiadiazole based heterocycles

Rizk E. KhidreChemical Industries Division, National Research Centre, Giza, Egypt; ;Chemistry Department, Faculty of Science, Jazan University, Jazan, Saudi Arabia; Correspondence[email protected]
ORCID Iconhttp://orcid.org/0000-0002-2317-8683
ORCID Icon,
Ibrahim Ali M. RadiniChemistry Department, Faculty of Science, Jazan University, Jazan, Saudi Arabia;
&
Diaa A. IbrahimChemistry Department, Faculty of Science, Jazan University, Jazan, Saudi Arabia; ;National Organization for Drug Control & Research, Giza, EgyptORCID Iconhttp://orcid.org/0000-0001-6355-1158
ORCID Icon
Pages 1040-1047 | Received 21 Dec 2018, Accepted 03 Feb 2019, Published online: 09 Apr 2019
 
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Abstract

The reaction of 3-oxopropanenitriles with phenyl isothiocyanate in DMF containing KOH afforded the corresponding potassium salts. The latter salts were converted into ketene N,S-acetals upon acidification with hydrogen chloride. The reaction of the ketene N,S-acetals with 2-bromo-1-[5-methyl-1-(p-tolyl)-1H-1,2,3-triazol-4-yl]ethan-1-one or 3-(2-bromoacetyl)-2H-chromen-2-one gave novel thiophenes in good yields. Treatment of the ketene N,S-acetals with hydrazonyl halides afforded 1,3,4-thiadiazoles in good yields. The stereochemistry of the synthesized compounds was studied.

Graphical Abstract

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