RESUMO
A facile transition-metal-free synthesis of 3,5-bis(het)aryl/arylaminothiadiazoles has been reported. The overall protocol involves base-mediated tandem thioacylation of amidines with dithioesters or aryl isothiocyanates in DMF solvent and subsequent in situ intramolecular dehydrogenative N-S bond formation of thioacylamidine intermediates under an inert atmosphere. A probable mechanism involving a carbamoyl anion, generated by deprotonation of DMF, acting as a radical initiator has been suggested.
RESUMO
Single crystal XRD structure of the title compound reveals that the molecule adopt non-planar structure. The molecule is puckered with the total puckering amplitude of (Q) = 0.368(3)Å. Crystals of the title molecules are interconnected by intermolecular O-Hâ¯O and C-Hâ¯O interactions to develop 1D chains extending infinitely along the crystallographic a-axis. The intermolecular interactions were explored by Hirshfeld surfaces and their associated fingerprint graphs are obtained which revealed that the Hâ¯H and Hâ¯C pairs of inter atomic contacts were pre-dominant in the crystal packing of title compound. The energy of intermolecular interactions are computed using the accurate energy density model of B3LYP/6-31 G(d,p).