A new synthesis of 1 by selective deacetylation of 2 is reported. The acylation step implied in earlier syntheses of 1 and related compounds is exemplified by direct acylations of 3 to give 4a and 46. Several new 2-acylidene-3-(2,4-dibromophenyl)-5-phenyI-2,3-dihydro-1,3,4-thiadiazoles (11) and thioacylidene analogues (12) are described. The crystal structures of l l a , l l b , l l c , and l l d reveal a hypervalent interaction, ca. 2.45-2.7 A long, between the sulfur and carbonyl oxygen atoms. The dibromophenyl ring is nearly perpendicular to the thiadiazole ring plane in the crystal structures, and NMR data suggest that this conformation is maintained in solution. Molecular mechanics calculations show that the S...O interaction need only be a few kilocalories in order to_ stabilize the observed acylidene side chain configuration over other pcssible isomers. Crystals of l l a are triclinic, P1, with cell dimensions a = 12.937(2), b = 13.429(2), c = 13.489(2) A, a = 60.14(1)", P = 74.59 (1)
ChemInform is a weekly Abstracting Service, delivering concise information at a glance that was extracted from about 100 leading journals. To access a ChemInform Abstract of an article which was published elsewhere, please select a “Full Text” option. The original article is trackable via the “References” option.
scite is a Brooklyn-based organization that helps researchers better discover and understand research articles through Smart Citations–citations that display the context of the citation and describe whether the article provides supporting or contrasting evidence. scite is used by students and researchers from around the world and is funded in part by the National Science Foundation and the National Institute on Drug Abuse of the National Institutes of Health.