372. Synthetic antimalarials. Part XLIII. Some dithiobiurets and 1 : 2 : 4-triazoles related to “Paludrine.”

The Chemistry of 1,2,4-Triazoles.

“…A canonical form of the intermediate would be a highly reactive carbodiimide, which is known to react with water very readily, forming a substituted urea. 3-Amino-5-substituled-l,2,4-triaioles prepared from aminoguanidine and substituted aminoguanidine salts Other methods that are essentially variations of those discussed above are available and lead to 3-amino-5mercapto-(129, 131), 3,5-diamino- (95,103,168,350), and 3,5-dinitramino-l,2,4-triazoles (168).…”

Thioureas

“…At this point it dropped off, probably because of water insolubility. The search for antimalarials led to the testing of many substituted thioureas and pseudothioureas (52,97,163,196). However, none of these compounds have been reported to possess antimalarial activity.…”

“…Section II Section III (CHa)iNCSN(CH,), (131,195,247) (CjH«)(CiH()NCSN(CiHs)(C«Hi) (6) HiNCSNHCSNH, (5,59) CeHiNHCSNHCSNHi (59) -t-ClCeHiNHCSNHCSNHs 4-BrCsHiNHCSNHC (SC!H6)=NCsHt«) (52) 3-ClCeH4NHCSNHC(SC2H5)=NC.H7«) (52) 4-ClC.H4NHCSNHCSNHC3H7(«) (97) 4-C1C eHaNHC SNHCSNH (4-C1C sH4) (97) 4-C1CiH4NHCSNHC(SCH3)=N(4-C10«H4) (97) 4-C1CsH4NHCSNHC(SC!Hb)=NCHs (52) 4-C1C«H4NHCSNHC(SC2Hí)=NC!Hb (52) 4-CIC6H4NHCSNHC(SC=Hs)=NC1H7«) (52) 4-ClCtH4NHCSNHC (SCzHb)=NC4H, (52) 4-IC6H4NHCSNHC(SCíHb)=NC3H,U)…”

3-(Arylimino)-5-(phenylbenzylidenehydrazido)-1,2,4-dithiazolidines: oxidative debenzylation and cyclization of 1-(phenylbenzylideneamino)-5-aryl-2-S-benzyliso-4-thiobiurets

“…°Typical IR frequencies (cm'1) of 3-(phenylimino>5-(phenylbenzylidenehydrazido)• 1,2,4-dithiazolidine: C=N, 1620 (s); ring -S-Slinkage 480 (s); 3200 (m), N-H stretching. 6 All of these compounds gave elemental analysis (C, , N, S) within ±0.40% of the calculated values. substituted 2-S-benzyliso-4-thiobiuret made into paste with a little chloroform or carbon tetrachloride was treated with liquid bromine until the color of bromine persisted.…”