Utilization of N-aryl chloroacetamide reagents in the synthesis of new phenoxyacetamide, thiazolidin-4-one and thiophene derivatives

Document Type : Original Article

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Chemistry Department, Faculty of Science, Mansoura University, 35516 Mansoura, Egypt

Abstract

N-Aryl chloroacetamide derivatives (ArNHCOCH2Cl) were utilized as versatile precursors for the synthesis of various types of sulfides and phenoxy-acetamides, and two sulfur-containing heterocyclic systems (namely; thiophene and thiazole). The reaction of N-aryl chloroacetamides 1 with ethyl 2-mercaptoacetate furnished the conforming sulfide products 2a-e. Treatment of 1 with ammonium thiocyanate yielded the conforming 2-(arylimino)thiazolidin-4-ones 4a-e. Nucleophilic substitution of the chlorine atom from the N-aryl chloroacetamides 1 by the oxygen nucleophile of salicylaldehyde and/or 4-hydroxybenzaldehyde furnished the conforming 2-(formylphenoxy)-N-aryl-acetamides 5 and 6. The condensation reaction of 6b with thiosemicarbazide and/or N-(4-chlorophenyl)-2-cyanoacetamide yielded the expected products; thiosemicarbazone 7 and acrylamide 8, respectively. The reaction of 2-acetyl-3-oxo-N-phenylbutanethioamide (9) with chloroacetamide and/or N-aryl chloroacetamides 1 was explored in sodium ethoxide and the products were identified as 4-acetyl-5-(phenylamino)thiophenes 11 and 12. While, when the reaction carried out in boiling ethanol and triethylamine, the cyclization behaved opposite direction to produce 3-(5-oxo-3-phenylthiazolidin-2-ylidene)pentane-2,4-dione (13).

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