Decyanation of tertiary nitriles by alkyllithium reagents observed during the synthesis of imidazoles pendant to a quaternary carbon center

We have devised a five-step synthesis of the new chemical entities 7a-d from 5-methoxytetralone, 1, via unsaturated nitrile, the reductive alkylation products 4a-d, and ketones 5a-d and 6a-d. Structures 7a-d are distinguished by the presence of a 4-imidazolyl moiety pendant to a quaternary center of the 1,2,3,4-tetrahydronaphthalene nucleus. Synthetically, it is preferable to use CH 3 MgBr in benzene in the conversion of 4a-d to 5a-d