Abstract
A straightforward one-pot route for the synthesis of a new 4-phenyl-1,2,5,6-tetraazafluoranthen-3(2H)-one is reported form the direct hydrazinolysis of triketo ester and hydrazine hydrate in ethanol. 4-Phenyl-1,2,5,6-tetraazafluoranthen-3(2H)-one was subjected to aza-Michael addition and N-alkylation on reaction with a set of alkylating agents in the presence of K2CO3. Hydrazinolysis of 4-phenyl-1,2,5,6-tetraazafluoranthen-3(2H)-one ester to hydrazide and conversion of hydrazide to thiosemicarbazide were successful. X-Ray single crystals analysis and H-1, C-13 NMR were used for unambiguous structure confirmation. The O horizontal ellipsis H, N horizontal ellipsis H, C horizontal ellipsis N and C horizontal ellipsis C in 2, and the N horizontal ellipsis H, C horizontal ellipsis N, C horizontal ellipsis C, C horizontal ellipsis O and H horizontal ellipsis H interactions in 6 are the most important in the molecular packing based on Hirshfled analysis. Moreover, the presence of short C horizontal ellipsis C and C horizontal ellipsis N contacts in both compounds revealed the presence of pi-pi stacking interactions.