Synthesis and characterization of 5-amino-1,3,4-thiadiazole-2-sulfonamide based acridine compounds containing carbamate, sulfonamide, sulfonate groups

4-Nitro-N-(5-sulfamoyl-1,3,4-thiadiazol-2-yl)benzamide (IV) compound is obtained in high yield by interacting 5-amino-1,3,4-thiadiazole-2-sulfonamide and p-nitro benzoyl chloride (III) in tetrahydrofuran at room temperature. Then the compound is reduced in the presence of sodium poly-sulfur in ethanol–water. As a result of the reduction, 4-amino-N- (5-sulfamoyl-1,3,4-thiadiazol-2-yl)benzamide compound (V) is obtained. Firstly, novel hybrid-acridine derivatives (IX (a-e), XII (a-d)) were synthesized by the reaction among obtained new amine compound (V), dimedone (13) and sulfonate ester or carbamate compounds containing aromatic aldehydes (VIII (a-e)-XI (a-d)) with assisted microwave irritation. Secondly, novel nitro-acridine compound (XIV) was synthesized from the reaction of dimedone (13), new amine compound (V) and p-nitro benzaldehyde (XIII). Then the compound (XIV) was reduced in the presence of sodium poly-sulfur in ethanol–water. Novel acridine-sulfonamide derivatives (XVI (a-i)) were synthesized by the reaction of these reduced product (XV) with various sulfonyl chlorides and carbamoyl chlorides. The structures of the synthesized compounds were elucidated by FT-IR, 1H-NMR, 13C-NMR (APT) and HRMS spectral techniques.