4‐Toluenesulfonamide as a Building Block for Synthesis of Novel Triazepines, Pyrimidines, and Azoles

• Published in: Journal of heterocyclic chemistry 2016-09, Vol.53 (5), p.1544-1553
• Main Authors: Khodairy, A., Ali, Ali M., El‐Wassimy, M. T.
• Format: Article
• Language: English
• ISSN: 0022-152X; 1943-5193
• DOI: 10.1002/jhet.2461

N‐{(E)‐(dimethylamino)methylidenearbamothioyl}‐4‐toluenesulfonamide (2) was obtained by reaction of N‐carbamothioyl‐4‐toluenesulfonamide (1) with dimethylformamide dimethylacetal or alternatively by the reaction of 1‐(dimethylamino)methylidenethiourea with tosyl chloride. Compound 2 was reacted with substituted anilines to yield anilinomethylidine derivatives 3a, 3b, 3c, 3d, 3e, 3f, 3g. Treatment of 3a, 3b, 3c, 3d, 3e, 3f, 3g with phenacyl bromide gave triazepines 4a, 4b, 4c, 4d, 4e, 4f, 4g and imidazoles 5a, 5b, 5c, 5d, 5e, 5f, 5g. Esterification of compound 3e afforded ester derivative 6, which was subjected to react with hydrazine to yield hydrazide derivative 7. Oxadiazole 8 was obtained by reaction of 7 with CS2/KOH. Compound 3e was treated with o‐aminophenol or o‐aminothiophenol to give benzazoles 9a, 9b. N‐(Diaminomethylidene)‐4‐toluenesulfonamide (10) reacted with enaminones to yield pyrimidines 11, 12, 13, respectively. The structures of the compounds were elucidated by elemental and spectral analyses. Some selected compounds were screened for their in vitro antifungal activity. In general, the newly synthesized compounds showed good antifungal activity.