Utility of N‐[4‐(N‐Substituted Sulfamoyl)Phenyl] Cyanothioformamides in the Synthesis of Heterocyclic Compounds

Abstract

The novel cyanothioformamides 2a-d were prepared by treatment of isothiocyanatosulfonamides 1a-d with potassium cyanide at room temperature. Cyclocondensation of compounds 2b,c with phenyl isocyanate as electrophile furnished the corresponding imidazolidines 3a,b. The reactivity of compound 3a towards some nitrogen nucleophiles was investigated. Thus, the thiosemicarbazone 4 and imidazo[4,5-b]quinoxaline 6 were synthesized by condensation of compound 3a with thiosemicarbazide and o-phenylenediamine, respectively. Treatment of 3a with hydrochloric acid afforded compound 7. Our investigation was extended to include the reactivity of cyanothioformamide 2 towards o-aminophenol, anthranilic acid, and o-phenylenediamine and yielded the corresponding heterocycles 9, 11 and 13 derivatives, respectively. Structures of the synthesized compounds were established by their elemental analysis and spectral data.

Synthesis and Biological Evaluation of Bis‐Imidazolidineiminothiones: A Comparative Study

“…Interestingly, aromatic cyanothioformanilides are themselves bioactive and have been reported to exhibit a wide spectrum of bioactivity . Several classical methods as well as more recent eco‐friendly protocols have been reported in the literature for the preparation of such compounds.…”

Thiosemicarbazides in heterocyclization

“…The reaction of acetylpyrazines 1a , 1b , 1c , 1d , 1e , 1f , 1g with N,N ‐dimethylthiosemicarbazide 1 yielded the final thiosemicarbazones 12a , 12b , 12c , 12d , 12e , 12f , 12g [18, 19]. Analogous acetophenone N,N ‐dimethylthiosemicarbazone 13 was prepared for comparison in the same synthetic way [20–22].…”

“…Thiosemicarbazone derivative 17 was produced by treatment of compound 16 with thiosemicarbazide 1 under reflux in absolute ethanol, via elimination of hydrogen sulfide [19]. …”

Determination and Temperature Dependence of n-Octanol/Water Partition Coefficients for Seven Sulfonamides from (298.15 to 333.15) K

“…Subsequently, the potential exists for quantities of these drugs to be excreted as the parent compound and/or metabolites and enter the environment due to the spreading of manure and slurry on agricultural land, or direct deposition by grazing livestock. [1][2][3] The fundamental research for their environmental behavior evaluation, biological activity mechanics, interaction mechanics between drug molecules and receptor molecules, and designing new sulfanilamide in the molecular level, is eager to be proceeded. The n-octanol/water partition coefficient (P ow ), which is the quantitative parameter for accessing the interaction between drug and biofilm, 4,5 is one of the most important parameters employed for estimating a chemical's environmental fate and toxicity.…”