Oxadiazole derivatives R 0290Synthesis of Secondary and Tertiary Aminofurazans. -The reaction of nitrofurazans like (I) and (XIII) with primary and secondary amines proceeds with substitution of the nitro group to furnish the secondary and tertiary title aminofurazans. A wide range of side reactions is observed, and the reaction conditions must be optimized for each substrate. A further expansion of the spectrum furazans is presented by reactions using the amidoxime fragment as in (XVI). -(SHEREMETEV*, A. B.; ANDRIANOV, V. G.; MANTSEVA, E. V.; SHATUNOVA, E. V.; ALEKSANDROVA, N. S.; YUDIN, I. L.; DMITRIEV, D. E.; AVERKIEV, B. B.; ANTIPIN, M. Y.; Russ.
Nucleophilic Substitution in the Furazan Series. Reactions with O-Nucleophiles.-Nitrofurazans serve as excellent synthons in the preparation of hydroxyfurazans as well as furazanyl ethers. Hydroxylation of nitrofurazans is smoothly achieved on reaction with NaOH. It is shown that the selective substitution of one nitro group in dinitrofurazan (VII) and dinitro(aza)difurazan analogues is difficult to achieve and is accompanied by disubstitution as well as formation of difurazanyl ethers [cf. (X)]. Reaction of nitrofurazans with alcoholates (III) or phenolates (V) provides access to a wide range of furazanyl ethers (IV) and (VI), respectively. -(SHEREMETEV, A. B.; KHARITONOVA, O. V.; MANTSEVA, E. V.; KULAGINA, V. O.; SHATUNOVA, E. V.; ALEKSANDROVA, N. S.; MEL'NIKOVA, T. M.; IVANOVA, E. A.; DMITRIEV, D. E.; EMAN, V.; ET AL.; Russ. J. Org.
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.