Donor–Acceptor Cyclopropane Ring Opening with 6-Amino-1,3-dimethyluracil and Its Use in Pyrimido[4,5-<i>b</i>]azepines Synthesis
Anna E. Vartanova, Ирина И. Левина, Victor B. Rybakov, Оlga А. Ivanova, Igor V. Trushkov
Abstract
A scandium trifluoromethanesulfonate-catalyzed reaction of donor–acceptor cyclopropanes with 6-amino-1,3-dimethyluracil was found to proceed as three-membered ring opening via nucleophilic attack of the C(5) atom of an ambident nucleophile serving as an enamine equivalent. It was shown that, under basic conditions, the obtained products underwent cyclization to 6,7-dihydro-1H-pyrimido[4,5-b]azepine-2,4,8-triones, an interesting subclass of nucleobase analogues.
Topics & Concepts
ChemistryNucleophileAzepineRing (chemistry)CyclopropaneTrifluoromethanesulfonateScandiumElectrophileEnamineAcceptorNucleobaseStereochemistryMedicinal chemistryIminiumNitrileCatalysisCombinatorial chemistryOrganic chemistryDNABiochemistryPhysicsCondensed matter physicsCyclopropane Reaction MechanismsSynthesis and Catalytic ReactionsSynthesis and Reactivity of Heterocycles