Synthesis of a Novel Hydrazone of Thieno[2,3-d]pyrimidine Clubbed with Ninhydrin: X-ray Crystal Structure and Computational Investigations

The novel hydrazone-containing thieno[2,3-d]pyrimidine, namely, N′-(1,3-dioxo-1,3-dihydro-2H-inden-2-ylidene)-2-(4-oxo-5,6,7,8-tetrahydrobenzo[4,5]thieno[2,3-d]pyrimidin-3(4H)-yl)acetohydrazide 4 was synthesized in a very good yield from the reaction of triketoester 1 or ninhydrin 2 with exocyclic acetohydrazide 3 methanol. Good-quality crystals were obtained by recrystallization compound DMF/MeOH solvent mixture. target product crystallized triclinic crystal system and P-1 space group. topology analysis molecular packing indicated that H…H (30.4%), O…H (22.0%) H…C (17.0%) contacts are most dominant intermolecular interactions 4, while O…H, N…H, H…C, N…C, O…C, C…C O…O only which have shorter interaction distances than vdWs radii sum interacting atoms. structure is optimized calculated showed agreement experimental one. Additionally, MEP, HOMO, LUMO reactivity descriptors calculated.